Condensed cyclic compound and organic light-emitting device including the same

ABSTRACT

A condensed cyclic compound represented by Formula 1: 
     
       
         
         
             
             
         
       
         
         
           
             wherein, in Formula 1, groups and variables are the same as described in the specification.

CROSS-REFERENCE TO RELATED APPLICATION

This application is a continuation application of U.S. patentapplication Ser. No. 15/234,089, filed on Aug. 11, 2016, which claimspriority to and the benefit of Korean Patent Application No.10-2015-0114548, filed on Aug. 13, 2015, in the Korean IntellectualProperty Office, the contents of which are incorporated herein in theirentirety by reference.

BACKGROUND 1. Field

The present disclosure relates to a condensed cyclic compound and anorganic light-emitting device including the condensed cyclic compound.

2. Description of the Related Art

Organic light-emitting devices (OLEDs) are self-emission devices thathave wide viewing angles, high contrast ratios, and short responsetimes. In addition, the OLEDs exhibit excellent luminance, drivingvoltage, and response speed characteristics, and produce full-colorimages.

A typical organic light-emitting device includes an anode, a cathode,and an organic layer that is disposed between the anode and the cathodeand includes an emission layer. A hole transport region may be disposedbetween the anode and the emission layer, and an electron transportregion may be disposed between the emission layer and the cathode. Holesprovided from the anode may move toward the emission layer through thehole transport region, and electrons provided from the cathode may movetoward the emission layer through the electron transport region. Theholes and the electrons recombine in the emission layer to produceexcitons. These excitons change from an excited state to a ground stateto thereby generate light.

Different types of organic light emitting devices are known. However,there still remains a need in OLEDs having low driving voltage, highefficiency, high brightness, and long lifespan.

SUMMARY

Provided are a condensed cyclic compound and an organic light-emittingdevice including the condensed cyclic compound.

Additional aspects will be set forth in part in the description whichfollows and, in part, will be apparent from the description, or may belearned by practice of the presented exemplary embodiments.

According to an aspect of an exemplary embodiment, provided is acondensed cyclic compound represented by Formula 1:

wherein, in Formula 1,

-   -   X₁ may be selected from a single bond, O, S, N(R₁₁) and        C(R₁₂)(R₁₃),    -   X₂ may be O or S,    -   ring A₁ to ring A₄ may each independently be a C₅-C₆₀        carbocyclic group or a C₂-C₆₀ heterocyclic group,    -   ring A₅ may be selected from a benzene, a pyridine, a        pyrimidine, a pyrazine, a pyridazine and a triazine,    -   R₁ to R₆ and R₁₁ to R₁₃ may be each independently selected from        a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a        cyano group, a nitro group, an amino group, an amidino group, a        hydrazine group, a hydrazone group, a carboxylic acid group or a        salt thereof, a sulfonic acid group or a salt thereof, a        phosphoric acid group or a salt thereof, a substituted or        unsubstituted C₁-C₆₀ alkyl group, a substituted or unsubstituted        C₂-C₆₀ alkenyl group, a substituted or unsubstituted C₂-C₆₀        alkynyl group, a substituted or unsubstituted C₁-C₆₀ alkoxy        group, a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, a        substituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, a        substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a        substituted or unsubstituted C₁-C₁₀ heterocycloalkenyl group, a        substituted or unsubstituted C₆-C₆₀ aryl group, a substituted or        unsubstituted C₆-C₆₀ aryloxy group, a substituted or        unsubstituted C₆-C₆₀ arylthio group, a substituted or        unsubstituted C₇-C₆₀ arylalkyl group, a substituted or        unsubstituted C₁-C₆₀ heteroaryl group, a substituted or        unsubstituted C₁-C₆₀ heteroaryloxy group, a substituted or        unsubstituted C₁-C₆₀ heteroarylthio group, a substituted or        unsubstituted C₂-C₆₀ heteroarylalkyl group, a substituted or        unsubstituted monovalent non-aromatic condensed polycyclic        group, a substituted or unsubstituted monovalent non-aromatic        condensed heteropolycyclic group, —Si(Q₁)(Q₂)(Q₃), —N(Q₄)(Q₅)        and —B(Q₆)(Q₇),    -   a1 may be an integer of 1 to 4,    -   a2 to a6 may be each independently an integer of 0 to 4,    -   L₁ may be selected from    -   a phenylene group, a pyridinylene group, a pyrimidinylene group,        a pyrazinylene group, a pyridazinylene group and a triazinylene        group; and    -   a phenylene group, a pyridinylene group, a pyrimidinylene group,        a pyrazinylene group, a pyridazinylene group and a triazinylene        group, each substituted with at least one selected from a        deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a        nitro group, an amino group, an amidino group, a hydrazine        group, a hydrazone group, a carboxylic acid group or a salt        thereof, a sulfonic acid group or a salt thereof, a phosphoric        acid group or a salt thereof, a C₁-C₁₀ alkyl group, a C₁-C₁₀        alkoxy group, a phenyl group, a naphthyl group, a pyridinyl        group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl        group, a triazinyl group and —Si(Q₈)(Q₉)(Q₁₀),    -   b1 may be an integer of 1 to 3,    -   n may be an integer of 0 to 3,    -   the number of cyano groups in Formula 1 may be 1, 2, 3 or 4,    -   at least one substituent of the substituted C₁-C₆₀ alkyl group,        substituted C₂-C₆₀ alkenyl group, substituted C₂-C₆₀ alkynyl        group, substituted C₁-C₆₀ alkoxy group, substituted C₃-C₁₀        cycloalkyl group, substituted C₁-C₁₀ heterocycloalkyl group,        substituted C₃-C₁₀ cycloalkenyl group, substituted C₁-C₁₀        heterocycloalkenyl group, substituted C₆-C₆₀ aryl group,        substituted C₆-C₆₀ aryloxy group, substituted C₆-C₆₀ arylthio        group, substituted C₇-C₆₀ arylalkyl group, substituted C₁-C₆₀        heteroaryl group, substituted C₁-C₆₀ heteroaryloxy group,        substituted C₁-C₆₀ heteroarylthio group, substituted C₂-C₆₀        heteroarylalkyl group, substituted monovalent non-aromatic        condensed polycyclic group and substituted monovalent        non-aromatic condensed heteropolycyclic group may be selected        from    -   a deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H,        —CFH₂, a hydroxyl group, a cyano group, a nitro group, an amino        group, an amidino group, a hydrazine group, a hydrazone group, a        carboxylic acid group or a salt thereof, a sulfonic acid group        or a salt thereof, a phosphoric acid group or a salt thereof, a        C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl        group and a C₁-C₆₀ alkoxy group;    -   a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl        group and a C₁-C₆₀ alkoxy group, each substituted with at least        one selected from a deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H,        —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a        nitro group, an amino group, an amidino group, a hydrazine        group, a hydrazone group, a carboxylic acid group or a salt        thereof, a sulfonic acid group or a salt thereof, a phosphoric        acid group or a salt thereof, a C₃-C₁₀ cycloalkyl group, a        C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a        C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀        aryloxy group, a C₆-C₆₀ arylthio group, a C₇-C₆₀ arylalkyl        group, a C₁-C₆₀ heteroaryl group, a C₁-C₆₀ heteroaryloxy group,        a C₁-C₆₀ heteroarylthio group, a C₂-C₆₀ heteroarylalkyl group, a        monovalent non-aromatic condensed polycyclic group, a monovalent        non-aromatic condensed heteropolycyclic group,        —Si(Q₁₁)(Q₁₂)(Q₁₃), —N(Q₁₄)(Q₁₅) and —B(Q₁₆)(Q₁₇);    -   a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a        C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a        C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio        group, a C₇-C₆₀ arylalkyl group, a C₁-C₆₀ heteroaryl group, a        C₁-C₆₀ heteroaryloxy group, a C₁-C₆₀ heteroarylthio group, a        C₂-C₆₀ heteroarylalkyl group, a monovalent non-aromatic        condensed polycyclic group and a monovalent non-aromatic        condensed heteropolycyclic group;    -   a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a        C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a        C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio        group, a C₇-C₆₀ arylalkyl group, a C₁-C₆₀ heteroaryl group, a        C₁-C₆₀ heteroaryloxy group, a C₁-C₆₀ heteroarylthio group, a        C₂-C₆₀ heteroarylalkyl group, a monovalent non-aromatic        condensed polycyclic group and a monovalent non-aromatic        condensed heteropolycyclic group, each substituted with at least        one selected from a deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H,        —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a        nitro group, an amino group, an amidino group, a hydrazine        group, a hydrazone group, a carboxylic acid group or a salt        thereof, a sulfonic acid group or a salt thereof, a phosphoric        acid group or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀        alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a        C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a        C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a        C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio        group, a C₇-C₆₀ arylalkyl group, a C₁-C₆₀ heteroaryl group, a        C₁-C₆₀ heteroaryloxy group, a C₁-C₆₀ heteroarylthio group, a        C₂-C₆₀ heteroarylalkyl group, a monovalent non-aromatic        condensed polycyclic group, a monovalent non-aromatic condensed        heteropolycyclic group, —Si(Q₂₁)(Q₂₂)(Q₂₃), —N(Q₂₄)(Q₂₅) and        —B(Q₂₆)(Q₂₇); and    -   —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₄)(Q₃₅) and —B(Q₃₆)(Q₃₇),    -   Q₁ to Q₁₀, Q₁₁ to Q₁₇, Q₂₁ to Q₂₇ and Q₃₁ to Q₃₇ may be each        independently selected from a hydrogen, a deuterium, —F, —Cl,        —Br, —I, a hydroxyl group, a cyano group, a nitro group, an        amino group, an amidino group, a hydrazine group, a hydrazone        group, a carboxylic acid group or a salt thereof, a sulfonic        acid group or a salt thereof, a phosphoric acid group or a salt        thereof, a substituted or unsubstituted C₁-C₆₀ alkyl group, a        substituted or unsubstituted C₂-C₆₀ alkenyl group, a substituted        or unsubstituted C₂-C₆₀ alkynyl group, a substituted or        unsubstituted C₁-C₆₀ alkoxy group, a substituted or        unsubstituted C₃-C₁₀ cycloalkyl group, a substituted or        unsubstituted C₁-C₁₀ heterocycloalkyl group, a substituted or        unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted or        unsubstituted C₁-C₁₀ heterocycloalkenyl group, a substituted or        unsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted        C₆-C₆₀ aryloxy group, a substituted or unsubstituted C₆-C₆₀        arylthio group, a substituted or unsubstituted C₇-C₆₀ arylalkyl        group, a substituted or unsubstituted C₁-C₆₀ heteroaryl group, a        substituted or unsubstituted C₁-C₆₀ heteroaryloxy group, a        substituted or unsubstituted C₁-C₆₀ heteroarylthio group, a        substituted or unsubstituted C₂-C₆₀ heteroarylalkyl group, a        substituted or unsubstituted monovalent non-aromatic condensed        polycyclic group and a substituted or unsubstituted monovalent        non-aromatic condensed heteropolycyclic group.

According to an aspect of another exemplary embodiment, provided is anorganic light-emitting device including:

-   -   a first electrode;    -   a second electrode; and    -   an organic layer disposed between the first electrode and the        second electrode,    -   wherein the organic layer includes an emission layer and at        least one condensed cyclic compound represented by Formula 1.

BRIEF DESCRIPTION OF THE DRAWINGS

These and/or other aspects will become apparent and more readilyappreciated from the following description of the exemplary embodiments,taken in conjunction with the accompanying drawings in which:

FIGURE illustrates a schematic view of an organic light-emitting deviceaccording to an embodiment.

DETAILED DESCRIPTION

Reference will now be made in detail to exemplary embodiments, examplesof which are illustrated in the accompanying drawings, wherein likereference numerals refer to like elements throughout. In this regard,the present exemplary embodiments may have different forms and shouldnot be construed as being limited to the descriptions set forth herein.Accordingly, the exemplary embodiments are merely described below, byreferring to the figures, to explain aspects of the present inventiveconcept. Expressions such as “at least one of,” when preceding a list ofelements, modify the entire list of elements and do not modify theindividual elements of the list.

It will be understood that when an element is referred to as being “on”another element, it can be directly in contact with the other element orintervening elements may be present therebetween. In contrast, when anelement is referred to as being “directly on” another element, there areno intervening elements present.

It will be understood that, although the terms first, second, third etc.may be used herein to describe various elements, components, regions,layers, and/or sections, these elements, components, regions, layers,and/or sections should not be limited by these terms. These terms areonly used to distinguish one element, component, region, layer, orsection from another element, component, region, layer, or section.Thus, a first element, component, region, layer, or section discussedbelow could be termed a second element, component, region, layer, orsection without departing from the teachings of the present embodiments.

The terminology used herein is for the purpose of describing particularembodiments only and is not intended to be limiting. As used herein, thesingular forms (“a,” “an,” and “the” are intended to include the pluralforms as well, unless the context clearly indicates otherwise.

The term “or” means “and/or.” It will be further understood that theterms “comprises” and/or “comprising,” or “includes” and/or “including”when used in this specification, specify the presence of statedfeatures, regions, integers, steps, operations, elements, and/orcomponents, but do not preclude the presence or addition of one or moreother features, regions, integers, steps, operations, elements,components, and/or groups thereof.

Unless otherwise defined, all terms (including technical and scientificterms) used herein have the same meaning as commonly understood by oneof ordinary skill in the art to which this general inventive conceptbelongs. It will be further understood that terms, such as those definedin commonly used dictionaries, should be interpreted as having a meaningthat is consistent with their meaning in the context of the relevant artand the present disclosure, and will not be interpreted in an idealizedor overly formal sense unless expressly so defined herein.

Exemplary embodiments are described herein with reference to crosssection illustrations that are schematic illustrations of idealizedembodiments. As such, variations from the shapes of the illustrations asa result, for example, of manufacturing techniques and/or tolerances,are to be expected. Thus, embodiments described herein should not beconstrued as limited to the particular shapes of regions as illustratedherein but are to include deviations in shapes that result, for example,from manufacturing. For example, a region illustrated or described asflat may, typically, have rough and/or nonlinear features. Moreover,sharp angles that are illustrated may be rounded. Thus, the regionsillustrated in the figures are schematic in nature and their shapes arenot intended to illustrate the precise shape of a region and are notintended to limit the scope of the present claims.

According to an aspect, provided is a condensed cyclic compoundrepresented by Formula 1:

X₁ in Formula 1 may be selected from a single bond, O, S, N(R₁₁) andC(R₁₂)(R₁₃), and X₂ may be O or S. Descriptions of R₁₁ to R₁₃ may beunderstood by referring to the descriptions below.

According to an embodiment, X₁ in Formula 1 may be a single bond, butembodiments are not limited thereto.

Ring A₁ to ring A₄ in Formula 1 may each independently be a C₅-C₆₀carbocyclic group or a C₂-C₆₀ heterocyclic group.

For example, ring A₁ to ring A₄ in Formula 1 may be each independentlyselected from a benzene, a pyridine, a pyrimidine, a pyrazine, apyridazine, a naphthalene, a quinoline, an isoquinoline, a quinoxaline,a quinazoline, a cinnoline, an indene, an indole, a benzofuran, abenzothiophene, a fluorene, a carbazole, a dibenzofuran and adibenzothiophene.

According to an embodiment, ring A₁ to ring A₄ in Formula 1 may be eachindependently selected from a benzene, a benzofuran, a benzothiophene, afluorene, a carbazole, a dibenzofuran and a dibenzothiophene.

In some embodiments, ring A₁ to ring A₄ in Formula 1 may be eachindependently selected from a benzene, a fluorene, a carbazole, adibenzofuran and a dibenzothiophene.

In some embodiments, ring A₁ to ring A₄ in Formula 1 may be eachindependently selected from a benzene, a fluorene, a carbazole, adibenzofuran and a dibenzothiophene, at least one of ring A₁ and ring A₂may be a benzene, and at least one of ring A₃ and ring A₄ may be abenzene.

In some embodiments, in Formula 1, ring A₁ and ring A₂ may be eachindependently selected from a benzene, a dibenzofuran and adibenzothiophene; ring A₃ and ring A₄ may be each independently selectedfrom a benzene, a fluorene, a carbazole, a dibenzofuran and adibenzothiophene; at least one of ring A₁ and ring A₂ may be a benzene;and at least one of ring A₃ and ring A₄ may be a benzene, butembodiments are not limited thereto.

Ring A₅ in Formula 1 may be selected from a benzene, a pyridine, apyrimidine, a pyrazine, a pyridazine and a triazine. For example, ringA₅ may be a benzene, but embodiments are not limited thereto.

R₁ to R₆ and R₁₁ to R₁₃ in Formula 1 may be each independently selectedfrom a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a substituted or unsubstituted C₁-C₆₀ alkylgroup, a substituted or unsubstituted C₂-C₆₀ alkenyl group, asubstituted or unsubstituted C₂-C₆₀ alkynyl group, a substituted orunsubstituted C₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀ heterocycloalkylgroup, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkenyl group, asubstituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstitutedC₆-C₆₀ arylthio group, a substituted or unsubstituted C₇-C₆₀ arylalkylgroup, a substituted or unsubstituted C₁-C₆₀ heteroaryl group, asubstituted or unsubstituted C₁-C₆₀ heteroaryloxy group, a substitutedor unsubstituted C₁-C₆₀ heteroarylthio group, a substituted orunsubstituted C₂-C₆₀ heteroarylalkyl group, a substituted orunsubstituted monovalent non-aromatic condensed polycyclic group, asubstituted or unsubstituted monovalent non-aromatic condensedheteropolycyclic group, —Si(Q₁)(Q₂)(Q₃), —N(Q₄)(Q₅) and —B(Q₆)(Q₇).

For example, R₁ to R₆ and R₁₁ to R₁₃ in Formula 1 may be eachindependently selected from

-   -   a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a        cyano group, a nitro group, an amino group, an amidino group, a        hydrazine group, a hydrazone group, a carboxylic acid group or a        salt thereof, a sulfonic acid group or a salt thereof, a        phosphoric acid group or a salt thereof, a C₁-C₂₀ alkyl group        and a C₁-C₂₀ alkoxy group;    -   a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, each substituted        with at least one selected from a deuterium, —F, —Cl, —Br, —I, a        hydroxyl group, a cyano group, a nitro group, an amino group, an        amidino group, a hydrazine group, a hydrazone group, a        carboxylic acid group or a salt thereof, a sulfonic acid group        or a salt thereof, a phosphoric acid group or a salt thereof, a        phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl        group, a pyrazinyl group, a pyridazinyl group, and a triazinyl        group;    -   a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group,        a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a        pentalenyl group, an indenyl group, a naphthyl group, an        azulenyl group, a heptalenyl group, an indacenyl group, an        acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group,        a phenalenyl group, a phenanthrenyl group, an anthracenyl group,        a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a        chrysenyl group, a naphthacenyl group, a picenyl group, a        perylenyl group, a pentaphenyl group, a hexacenyl group, a        pyrrolyl group, an imidazolyl group, a pyrazolyl group, a        pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a        pyridazinyl group, an isoindolyl group, an indolyl group, an        indazolyl group, a purinyl group, a quinolinyl group, an        isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl        group, a naphthyridinyl group, a quinoxalinyl group, a        quinazolinyl group, a cinnolinyl group, a phenanthridinyl group,        an acridinyl group, a phenanthrolinyl group, a phenazinyl group,        a benzoxazolyl group, a benzoimidazolyl group, a furanyl group,        a benzofuranyl group, a thiophenyl group, a benzothiophenyl        group, a thiazolyl group, an isothiazolyl group, a        benzothiazolyl group, an isoxazolyl group, an oxazolyl group, a        triazolyl group, a tetrazolyl group, an oxadiazolyl group, a        triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl        group, an imidazopyrimidinyl group and an imidazopyridinyl        group;    -   a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group,        a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a        pentalenyl group, an indenyl group, a naphthyl group, an        azulenyl group, a heptalenyl group, an indacenyl group, an        acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group,        a phenalenyl group, a phenanthrenyl group, an anthracenyl group,        a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a        chrysenyl group, a naphthacenyl group, a picenyl group, a        perylenyl group, a pentaphenyl group, a hexacenyl group, a        pyrrolyl group, an imidazolyl group, a pyrazolyl group, a        pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a        pyridazinyl group, an isoindolyl group, an indolyl group, an        indazolyl group, a purinyl group, a quinolinyl group, an        isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl        group, a naphthyridinyl group, a quinoxalinyl group, a        quinazolinyl group, a cinnolinyl group, a phenanthridinyl group,        an acridinyl group, a phenanthrolinyl group, a phenazinyl group,        a benzoxazolyl group, a benzoimidazolyl group, a furanyl group,        a benzofuranyl group, a thiophenyl group, a benzothiophenyl        group, a thiazolyl group, an isothiazolyl group, a        benzothiazolyl group, an isoxazolyl group, an oxazolyl group, a        triazolyl group, a tetrazolyl group, an oxadiazolyl group, a        triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl        group, an imidazopyrimidinyl group and an imidazopyridinyl        group, each substituted with at least one selected from a        deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a        nitro group, an amino group, an amidino group, a hydrazine        group, a hydrazone group, a carboxylic acid group or a salt        thereof, a sulfonic acid group or a salt thereof, a phosphoric        acid group or a salt thereof, a C₁-C₂₀ alkyl group, a C₂-C₂₀        alkenyl group, a C₂-C₂₀ alkynyl group, a C₁-C₂₀ alkoxy group, a        phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl        group, a phenanthrenyl group, a fluorenyl group, a pyridinyl        group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl        group, a triazinyl group, a quinolinyl group, an isoquinolinyl        group, a phthalazinyl group, a quinoxalinyl group, a cinnolinyl        group, a quinazolinyl group and —Si(Q₃₁)(Q₃₂)(Q₃₃); and    -   —Si(Q₁)(Q₂)(Q₃),    -   wherein Q₁ to Q₃ and Q₃₁ to Q₃₃ may be each independently        selected from a hydrogen, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy        group, a phenyl group, a naphthyl group, an anthracenyl group, a        pyrenyl group, a phenanthrenyl group, a fluorenyl group, a        pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a        pyridazinyl group, a triazinyl group, a quinolinyl group, an        isoquinolinyl group a phthalazinyl group, a quinoxalinyl group,        a cinnolinyl group and a quinazolinyl group.

According to an embodiment, R₁ to R₆ and R₁₁ to R₁₃ in Formula 1 may beeach independently selected from

-   -   a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a        cyano group, a nitro group, an amino group, an amidino group, a        hydrazine group, a hydrazone group, a carboxylic acid group or a        salt thereof, a sulfonic acid group or a salt thereof, a        phosphoric acid group or a salt thereof, a C₁-C₁₀ alkyl group        and a C₁-C₁₀ alkoxy group;    -   a C₁-C₁₀ alkyl group and a C₁-C₁₀ alkoxy group, each substituted        with at least one selected from a deuterium, —F, —Cl, —Br, —I, a        hydroxyl group, a cyano group, a nitro group, an amino group, an        amidino group, a hydrazine group, a hydrazone group, a        carboxylic acid group or a salt thereof, a sulfonic acid group        or a salt thereof and a phosphoric acid group or a salt thereof;    -   a phenyl group, a naphthyl group, a pyridinyl group, a        pyrimidinyl group, a pyrazinyl group, a pyridazinyl group and a        triazinyl group;    -   a phenyl group, a naphthyl group, a pyridinyl group, a        pyrimidinyl group, a pyrazinyl group, a pyridazinyl group and a        triazinyl group, each substituted with at least one selected        from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano        group, a nitro group, an amino group, an amidino group, a        hydrazine group, a hydrazone group, a carboxylic acid group or a        salt thereof, a sulfonic acid group or a salt thereof, a        phosphoric acid group or a salt thereof, a C₁-C₁₀ alkyl group, a        C₁-C₁₀ alkoxy group, a phenyl group, a naphthyl group, a        pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a        pyridazinyl group, a triazinyl group and —Si(Q₃₁)(Q₃₂)(Q₃₃); and    -   —Si(Q₁)(Q₂)(Q₃),    -   wherein Q₁ to Q₃ and Q₃₁ to Q₃₃ may be each independently        selected from a hydrogen, a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy        group, a phenyl group, a naphthyl group, a pyridinyl group, a        pyrimidinyl group, a pyrazinyl group, a pyridazinyl group and a        triazinyl group, but embodiments are not limited thereto.

In some embodiments, R₁ to R₆ and R₁₁ to R₁₃ in Formula 1 may be eachindependently selected from

-   -   a hydrogen, a deuterium, a cyano group, a C₁-C₁₀ alkyl group and        a C₁-C₁₀ alkoxy group;    -   a C₁-C₁₀ alkyl group and a C₁-C₁₀ alkoxy group, each substituted        with at least one selected from a deuterium and a cyano group;    -   a phenyl group, a pyridinyl group, a pyrimidinyl group and a        triazinyl group;    -   a phenyl group, a pyridinyl group, a pyrimidinyl group and a        triazinyl group, each substituted with at least one selected        from a deuterium, a cyano group, a C₁-C₁₀ alkyl group, a C₁-C₁₀        alkoxy group, a phenyl group, a pyridinyl group, a pyrimidinyl        group, a triazinyl group and —Si(Q₃₁)(Q₃₂)(Q₃₃); and    -   —Si(Q₁)(Q₂)(Q₃),    -   wherein Q₁ to Q₃ and Q₃₁ to Q₃₃ may be each independently        selected from a hydrogen, a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy        group, a phenyl group, a pyridinyl group, a pyrimidinyl group        and a triazinyl group.

a1 in Formula 1 denotes the number of R_(1(s)) and may be an integer of1 to 4. When a1 is 2 or more, two or more R_(1(s)) may be the same ordifferent. Descriptions of a2 to a6 may be understood by referring tothe description of a1 and Formula 1.

a1 in Formula 1 may be an integer of 1 to 4 and a2 to a6 in Formula 1may each independently be an integer of 0 to 4. For example, a1 inFormula 1 may be 1, 2 or 3 and a2 to a6 in Formula 1 may eachindependently be 0, 1, 2 or 3.

L₁ in Formula 1 may be selected from

-   -   a phenylene group, a pyridinylene group, a pyrimidinylene group,        a pyrazinylene group, a pyridazinylene group and a triazinylene        group; and    -   a phenylene group, a pyridinylene group, a pyrimidinylene group,        a pyrazinylene group, a pyridazinylene group and a triazinylene        group, each substituted with at least one selected from a        deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a        nitro group, an amino group, an amidino group, a hydrazine        group, a hydrazone group, a carboxylic acid group or a salt        thereof, a sulfonic acid group or a salt thereof, a phosphoric        acid group or a salt thereof, a C₁-C₁₀ alkyl group, a C₁-C₁₀        alkoxy group, a phenyl group, a naphthyl group, a pyridinyl        group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl        group, a triazinyl group and —Si(Q₈)(Q₉)(Q₁₀).

For example, L₁ in Formula 1 may be selected from

-   -   a phenylene group, a pyridinylene group, a pyrimidinylene group        and a triazinylene group; and    -   a phenylene group, a pyridinylene group, a pyrimidinylene group        and a triazinylene group, each substituted with at least one        selected from a deuterium, a cyano group, a C₁-C₁₀ alkyl group,        a C₁-C₁₀ alkoxy group, a phenyl group, a pyridinyl group, a        pyrimidinyl group, a triazinyl group and —Si(Q₈)(Q₉)(Q₁₀),    -   wherein Q₈ to Q₁₀ may be each independently selected from a        hydrogen, a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, a phenyl        group, a pyridinyl group, a pyrimidinyl group and a triazinyl        group, but embodiments are not limited thereto.

According to an embodiment, L₁ in Formula 1 may be selected from groupsrepresented by Formulae 3-1 to 3-40:

In Formulae 3-1 to 3-40,

-   -   Z₁ may be selected from a hydrogen, a deuterium, —F, —Cl, —Br,        —I, a hydroxyl group, a cyano group, a nitro group, an amino        group, an amidino group, a hydrazine group, a hydrazone group, a        carboxylic acid group or a salt thereof, a sulfonic acid group        or a salt thereof, a phosphoric acid group or a salt thereof, a        C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, a phenyl group, a        naphthyl group, a pyridinyl group, a pyrimidinyl group, a        pyrazinyl group, a pyridazinyl group, a triazinyl group and        —Si(Q₈)(Q₉)(Q₁₀) (for example, a hydrogen, a deuterium, a cyano        group, a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, a phenyl        group, a pyridinyl group, a pyrimidinyl group, a triazinyl group        and —Si(Q₈)(Q₉)(Q₁₀)),    -   Q₈ to Q₁₀ may be each independently selected from a hydrogen, a        C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, a phenyl group, a        pyridinyl group, a pyrimidinyl group and a triazinyl group,    -   d4 may be an integer of 0 to 4,    -   d3 may be an integer of 0 to 3,    -   d2 may be an integer of 0 to 2, and    -   each of * and *′ is a binding site to a neighboring atom.

According to an embodiment, at least one of groups L₁ in the number ofb1 may be selected from groups represented by Formulae 3-15 to 3-40.

In some embodiments, all of groups L₁ in the number of b1 may be eachindependently selected from groups represented by Formulae 3-15 to 3-40.

b1 in Formula 1 denotes the number of groups L₁ and may be integer of 1to 3. When b1 is 2 or more, two or more groups L₁ may be the same ordifferent.

According to an embodiment, a group represented by *-(L₁)_(b1)-*′ inFormula 1 may be selected from groups represented by Formulae 4-1 to4-39:

In Formula 4-1 to 4-39,

-   -   X₂₁ may be N or C(Z₂₁), X₂₂ may be N or C(Z₂₂), X₂₃ may be N or        C(Z₂₃), X₂₄ may be N or C(Z₂₄), X₃₁ may be N or C(Z₃₁), X₃₂ may        be N or C(Z₃₂), X₃₃ may be N or C(Z₃₃), X₃₄ may be N or C(Z₃₄),        X₄₁ may be N or C(Z₄₁), X₄₂ may be N or C(Z₄₂), X₄₃ may be N or        C(Z₄₃), X₄₄ may be N or C(Z₄₄), provided that all of X₂₁ to X₂₄        are not N, provided that all of X₃₁ to X₃₄ are not N, and        provided that all of X₄₁ to X₄₄ are not N,    -   Z₂₁ to Z₂₄, Z₃₁ to Z₃₄, and Z₄₁ to Z₄₄ may be each independently        selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a        hydroxyl group, a cyano group, a nitro group, an amino group, an        amidino group, a hydrazine group, a hydrazone group, a        carboxylic acid group or a salt thereof, a sulfonic acid group        or a salt thereof, a phosphoric acid group or a salt thereof, a        C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, a phenyl group, a        naphthyl group, a pyridinyl group, a pyrimidinyl group, a        pyrazinyl group, a pyridazinyl group, a triazinyl group and        —Si(Q₈)(Q₉)(Q₁₀) (for example, a hydrogen, a deuterium, a cyano        group, a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, a phenyl        group, a pyridinyl group, a pyrimidinyl group, a triazinyl group        and —Si(Q₈)(Q)(Q₁₀)),    -   Q₈ to Q₁₀ may be each independently selected from a hydrogen, a        C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, a phenyl group, a        pyridinyl group, a pyrimidinyl group and a triazinyl group, and    -   each of * and *′ is a binding site to a neighboring atom.

For example, in Formulae 4-1 to 4-39, X₂₁ may be C(Z₂₁), X₂₂ may beC(Z₂₂), X₂₃ may be C(Z₂₃), X₂₄ may be C(Z₂₄), X₃₁ may be C(Z₃₁), X₃₂ maybe C(Z₃₂), X₃₃ may be C(Z₃₃), X₃₄ may be C(Z₃₄), X₄₁ may be C(Z₄₁), X₄₂may be C(Z₄₂), X₄₃ may be C(Z₄₃), and X₄₄ may be C(Z₄₄).

In some embodiments, one of X₂₁ to X₂₄ in Formulae 4-1 to 4-3 may be N,and the others thereof may not be N.

n in Formula 1 denotes the number of groups represented by*-(L₁)_(b1)-(R₆)_(a6) and may be an integer of 0 to 3. For example, n inFormula 1 may be 0 or 1, but embodiments are not limited thereto.

The number of cyano groups in Formula 1 may be 1, 2, 3 or 4. Forexample, the number of cyano groups in Formula 1 may be 1 or 2, butembodiments are not limited thereto.

When the number of cyano groups in Formula 1 is 1, a cyano group inFormula 1 may be included in one of ring A₂, ring A₃, ring A₄, ring A₅,groups L₁ in the number of b1 and groups R₆ in the number of a6.

When the number of cyano groups in Formula 1 is 2, cyano groups inFormula 1 may be included in two of ring A₂, ring A₃, ring A₄, ring A₅,L₁ in the number of b1 and R₆ in the number of a6.

According to an embodiment, in Formula 1,

-   -   one to four of groups R₂ in the number of a2 may be each        independently a cyano group or a cyano group-substituted C₆-C₁₀        aryl group;    -   one to four of groups R₃ in the number of a3 may be each        independently a cyano group or a cyano group-substituted C₆-C₁₀        aryl group;    -   one to three of groups R₄ in the number of a4 may be each        independently a cyano group or a cyano group-substituted C₆-C₁₀        aryl group;    -   one to three of groups R₅ in the number of a5 may be each        independently a cyano group or a cyano group-substituted C₆-C₁₀        aryl group;    -   i) one or two of groups R₅ in the number of a5 and ii) one or        two of groups R₂ in the number of a2 may be each independently a        cyano group or a cyano group-substituted C₆-C₁₀ aryl group;    -   i) one or two of groups R₅ in the number of a5 and ii) one or        two of groups R₃ in the number of a3 may be each independently a        cyano group or a cyano group-substituted C₆-C₁₀ aryl group;    -   i) one or two of groups R₅ in the number of a5 and ii) one or        two of groups R₄ in the number of a4 may be each independently a        cyano group or a cyano group-substituted C₆-C₁₀ aryl group;    -   i) one or two of groups R₂ in the number of a2 and ii) one or        two of groups R₃ in the number of a3 may be each independently a        cyano group or a cyano group-substituted C₆-C₁₀ aryl group;    -   i) one or two of groups R₂ in the number of a2 and ii) one or        two of groups R₄ in the number of a4 may be each independently a        cyano group or a cyano group-substituted C₆-C₁₀ aryl group; or    -   i) one or two of groups R₃ in the number of a3 and ii) one or        two of groups R₄ in the number of a4 may be each independently a        cyano group or a cyano group-substituted C₆-C₁₀ aryl group.

Detailed examples of “a cyano group-substituted C₆-C₁₀ aryl group” asdescribed herein may include a phenyl group substituted with at leastone cyano group, but embodiments are not limited thereto.

A condensed cyclic compound represented by Formula 1 may be representedby one of Formulae 1A to 1H:

In Formulae 1A to 1H, 2A and 2B,

-   -   descriptions of X₁, X₂, ring A₁, ring A₂, ring A₅, R₁ to R₆, a1        to a6, L₁, b1 and n are the same as described herein,    -   ring A₃ may be selected from a benzene, a pyridine, a        pyrimidine, a pyrazine, a pyridazine, an indene, an indole, a        benzofuran, a benzothiophene, a fluorene, a carbazole, a        dibenzofuran and a dibenzothiophene,    -   ring A₆ may be represented by Formula 2A,    -   ring A₇ may be represented by Formula 2B,    -   X₄ may be selected from O, S, N(R_(4c)) and C(R_(4d))(R_(4e)),    -   descriptions of R_(4a) to R_(4e) are the same as the description        of R₄,    -   aa4 may be an integer of 0 to 3, and    -   ab4 may be an integer of 0 to 2.

According to an embodiment, in Formulae 1A to 1H,

-   -   X₁ may be a single bond,    -   ring A₁ and ring A₂ may be each independently selected from a        benzene, a fluorene, a carbazole, a dibenzofuran and a        dibenzothiophene, and at least one of ring A₁ and ring A₂ may be        a benzene,    -   ring A₃ in Formulae 1A to 1D may be each independently selected        from a benzene, a fluorene, a carbazole, a dibenzofuran and a        dibenzothiophene, and ring A₃ in Formulae 1E to 1H may be a        benzene,    -   ring A₅ may be a benzene,    -   R₁ to R₆ and R_(4a) to R_(4e) may be each independently selected        from    -   a hydrogen, a deuterium, a cyano group, a C₁-C₁₀ alkyl group and        a C₁-C₁₀ alkoxy group;    -   a C₁-C₁₀ alkyl group and a C₁-C₁₀ alkoxy group, each substituted        with at least one selected from a deuterium and a cyano group;    -   a phenyl group, a pyridinyl group, a pyrimidinyl group and a        triazinyl group;    -   a phenyl group, a pyridinyl group, a pyrimidinyl group and a        triazinyl group, each substituted with at least one selected        from a deuterium, a cyano group, a C₁-C₁₀ alkyl group, a C₁-C₁₀        alkoxy group, a phenyl group, a pyridinyl group, a pyrimidinyl        group, a triazinyl group and —Si(Q₃₁)(Q₃₂)(Q₃₃); and    -   —Si(Q₁)(Q₂)(Q₃),    -   a1 may be an integer of 1 to 3,    -   a2 to a6 may each independently be an integer of 0 to 3,    -   aa4 and ab4 may each independently be an integer of 0 to 2,    -   L₁ may be selected from    -   a phenylene group, a pyridinylene group, a pyrimidinylene group        and a triazinylene group; and    -   a phenylene group, a pyridinylene group, a pyrimidinylene group        and a triazinylene group, each substituted with at least one        selected from a deuterium, a cyano group, a C₁-C₁₀ alkyl group,        a C₁-C₁₀ alkoxy group, a phenyl group, a pyridinyl group, a        pyrimidinyl group, a triazinyl group and —Si(Q₈)(Q₉)(Q₁₀),    -   b1 may be 1 or 2, and    -   n may be 0 or 1,    -   wherein Q₁ to Q₃, Q₃₁ to Q₃₃, and Q₈ to Q₁₀ may be each        independently selected from a hydrogen, a C₁-C₁₀ alkyl group, a        C₁-C₁₀ alkoxy group, a phenyl group, a pyridinyl group, a        pyrimidinyl group and a triazinyl group.

In Formulae 1A to 1H,

-   -   one to three of groups R₂ in the number a2 may be each        independently a cyano group or a cyano group-substituted C₆-C₁₀        aryl group;    -   one to three of groups R₃ in the number of a3 may be each        independently a cyano group or a cyano group-substituted C₆-C₁₀        aryl group;    -   one to three of groups R₄ in the number of a4 (or, one to three        of groups R_(4a) in the number of aa4) may be each independently        a cyano group or a cyano group-substituted C₆-C₁₀ aryl group;    -   one to three of groups R₅ in the number of a5 may be each        independently a cyano group or a cyano group-substituted C₆-C₁₀        aryl group;    -   i) one or two of groups R₅ in the number of a5 and ii) one or        two of groups R₂ in the number of a2 may be each independently a        cyano group or a cyano group-substituted C₆-C₁₀ aryl group;    -   i) one or two of groups R₅ in the number of a5 and ii) one or        two of groups R₃ in the number of a3 may be each independently a        cyano group or a cyano group-substituted C₆-C₁₀ aryl group;    -   i) one or two of groups R₅ in the number of a5 and ii) one or        two of groups R₄ in the number of a4 (or, one or two of groups        R_(4a) in the number of aa4) may be each independently a cyano        group or a cyano group-substituted C₆-C₁₀ aryl group;    -   i) one or two of groups R₂ in the number of a2 and ii) one or        two of groups R₃ in the number of a3 may be each independently a        cyano group or a cyano group-substituted C₆-C₁₀ aryl group;    -   i) one or two of groups R₂ in the number of a2 and ii) one or        two of groups R₄ in the number of a4 (or, one or two of groups        R_(4a) in the number of aa4) may be each independently a cyano        group or a cyano group-substituted C₆-C₁₀ aryl group; or    -   i) one or two of groups R₃ in the number of a3 and ii) one or        two of groups R₄ in the number of a4 (or, one or two of groups        R_(4a) in the number of aa4) may be each independently a cyano        group or a cyano group-substituted C₆-C₁₀ aryl group.

For example, a condensed cyclic compound represented by Formula 1 may berepresented by one of Formulae 1-1 to 1-19:

In Formulae 1-1 to 1-19,

-   -   descriptions of X₁, X₂, ring A₅, R₁ to R₆, a1 to a6, L₁, b1 and        n are the same as described herein,    -   X₃ may be selected from O, S, N(R_(3c)) and C(R_(3d))(R_(3e)),    -   X₄ may be selected from O, S, N(R_(4c)) and C(R_(4d))(R_(4e)),    -   X₅ may be selected from O, S, N(R_(2c)) and C(R_(2d))(R_(2e)),    -   descriptions of R_(2a) to R_(2e) are the same as the description        of R₂,    -   descriptions of R_(3a) to R_(3e) are the same as the description        of R₃,    -   descriptions of R_(4a) to R_(4e) are the same as the description        of R₄,    -   aa2 and aa3 may be an integer of 0 to 2,    -   ab2 and ab3 may be an integer of 0 to 4,    -   aa4 may be an integer of 0 to 3, and    -   ab4 may be an integer of 0 to 2.

According to an embodiment, in Formulae 1-1 to 1-19,

-   -   X₁ may be a single bond,    -   X₃ may be selected from O, S, N(R_(3c)) and C(R_(3d))(R_(3e)),    -   X₄ may be selected from O, S, N(R_(4c)) and C(R_(4d))(R_(4e)),    -   X₅ may be O or S,    -   ring A₅ may be a benzene,    -   R₁ to R₆, R_(2a) to R_(2e), R_(3a) to R_(3e), and R_(4a) to        R_(4e) may be each independently selected from    -   a hydrogen, a deuterium, a cyano group, a C₁-C₁₀ alkyl group and        a C₁-C₁₀ alkoxy group;    -   C₁-C₁₀ alkyl group and C₁-C₁₀ alkoxy group, each substituted        with at least one selected from a deuterium and a cyano group;    -   a phenyl group, a pyridinyl group, a pyrimidinyl group and a        triazinyl group;    -   a phenyl group, a pyridinyl group, a pyrimidinyl group and a        triazinyl group, each substituted with at least one selected        from a deuterium, a cyano group, a C₁-C₁₀ alkyl group, a C₁-C₁₀        alkoxy group, a phenyl group, a pyridinyl group, a pyrimidinyl        group, a triazinyl group and —Si(Q₃₁)(Q₃₂)(Q₃₃); and    -   —Si(Q₁)(Q₂)(Q₃),    -   a1 may be an integer of 1 to 3,    -   a2 to a6 may each independently be an integer of 0 to 3,    -   L₁ may be selected from    -   a phenylene group, a pyridinylene group, a pyrimidinylene group        and a triazinylene group; and    -   a phenylene group, a pyridinylene group, a pyrimidinylene group        and a triazinylene group, each substituted with at least one        selected from a deuterium, a cyano group, a C₁-C₁₀ alkyl group,        a C₁-C₁₀ alkoxy group, a phenyl group, a pyridinyl group, a        pyrimidinyl group, a triazinyl group and —Si(Q₈)(Q₉)(Q₁₀),    -   b1 may be 1 or 2,    -   n may be 0 or 1, and    -   Q₁ to Q₃, Q₃₁ to Q₃₃, and Q₈ to Q₁₀ may be each independently        selected from a hydrogen, a C₁-C₁₀ alkyl group, a C₁-C₆₀ alkoxy        group, a phenyl group, a pyridinyl group, a pyrimidinyl group        and a triazinyl group.

In Formulae 1-1 to 1-19,

-   -   one to three of groups R₂ in the number of a2 (or, one to three        of groups R_(2b) in the number of ab2) may be each independently        a cyano group or a cyano group-substituted C₆-C₁₀ aryl group;    -   one to three of groups R₃ in the number of a3 (or, one to three        of groups R_(3b) in the number of ab3) may be each independently        a cyano group or a cyano group-substituted C₆-C₁₀ aryl group;    -   one to three of groups R₄ in the number of a4 (or, one to three        of groups R_(4a) in the number of aa4) may be each independently        a cyano group or a cyano group-substituted C₆-C₁₀ aryl group;    -   one to three of groups R₅ in the number of a5 may be each        independently a cyano group or a cyano group-substituted C₆-C₁₀        aryl group;    -   i) one or two of groups R₅ in the number of a5 and ii) one or        two of groups R₂ in the number of a2 (or, one or two of groups        R_(2b) in the number of ab2) may be each independently a cyano        group or a cyano group-substituted C₆-C₁₀ aryl group;    -   i) one or two of groups R₅ in the number of a5 and ii) one or        two of groups R₃ in the number of a3 (or, one or two of groups        R_(3b) in the number of ab3) may be each independently a cyano        group or a cyano group-substituted C₆-C₁₀ aryl group;    -   i) one or two of groups R₅ in the number of a5 and ii) one or        two of groups R₄ in the number of a4 (or, one or two of groups        R_(4a) in the number of aa4) may be each independently a cyano        group or a cyano group-substituted C₆-C₁₀ aryl group;    -   i) one or two of groups R₂ in the number of a2 (or, one or two        of groups R_(2b) in the number of ab2) and ii) one or two of        groups R₃ in the number of a3 (or, one or two of groups R_(3b)        in the number of ab3) may be each independently a cyano group or        a cyano group-substituted C₆-C₁₀ aryl group;    -   i) one or two of groups R₂ in the number of a2 (or, one or two        of groups R_(2b) in the number of ab2) and ii) one or two of        groups R₄ in the number of a4 (or, one or two of groups R_(4a)        in the number of aa4) may be each independently a cyano group or        a cyano group-substituted C₆-C₁₀ aryl group; or    -   i) one or two of groups R₃ in the number of a3 (or, one or two        of groups R_(3b) in the number of ab3) and ii) one or two of        groups R₄ in the number of a4 (or, one or two of groups R_(4a)        in the number of aa4) may be each independently a cyano group or        a cyano group-substituted C₆-C₁₀ aryl group.

In some embodiments, a condensed cyclic compound represented by Formula1 may be represented by Formulae 1(1) to 1(12):

Descriptions of X₁, X₂, ring A₁ to ring A₅, R₁ to R₆, L₁, b1 and n inFormulae 1(1) to 1(12) are the same as described herein, a1 may be aninteger of 1 to 3 and a2 to a6 may each independently be an integer of 0to 3.

For example, in Formulae 1(1) to 1(12),

-   -   X₁ may be a single bond,    -   ring A₁ and ring A₂ may be each independently selected from a        benzene, a fluorene, a carbazole, a dibenzofuran and a        dibenzothiophene, and at least one of ring A₁ and ring A₂ may be        a benzene,    -   ring A₃ and ring A₄ may be each independently selected from a        benzene, a fluorene, a carbazole, a dibenzofuran and a        dibenzothiophene, and at least one of ring A₃ and ring A₄ may be        a benzene,    -   ring A₅ may be a benzene,    -   R₁ to R₆ may be each independently selected from    -   a hydrogen, a deuterium, a C₁-C₁₀ alkyl group and a C₁-C₁₀        alkoxy group;    -   a C₁-C₁₀ alkyl group and a C₁-C₁₀ alkoxy group, each substituted        with at least one deuterium;    -   a phenyl group, a pyridinyl group, a pyrimidinyl group and a        triazinyl group;    -   a phenyl group, a pyridinyl group, a pyrimidinyl group and a        triazinyl group, each substituted with at least one selected        from a deuterium, a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, a        phenyl group, a pyridinyl group, a pyrimidinyl group, a        triazinyl group and —Si(Q₃₁)(Q₃₂)(Q₃₃); and    -   —Si(Q₁)(Q₂)(Q₃),    -   L₁ may be selected from    -   a phenylene group, a pyridinylene group, a pyrimidinylene group        and a triazinylene group; and    -   a phenylene group, a pyridinylene group, a pyrimidinylene group        and a triazinylene group, each substituted with at least one        selected from a deuterium, a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy        group, a phenyl group, a pyridinyl group, a pyrimidinyl group, a        triazinyl group and —Si(Q₈)(Q₉)(Q₁₀),    -   b1 may be 1 or 2,    -   n may be 0 or 1, and    -   Q₁ to Q₃, Q₃₁ to Q₃₃, and Q₈ to Q₁₀ may be each independently        selected from a hydrogen, a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy        group, a phenyl group, a pyridinyl group, a pyrimidinyl group        and a triazinyl group, but embodiments are not limited thereto.

The condensed cyclic compound may be one of Compounds 1 to 482 below,but embodiments are not limited thereto:

“Ring A” in the condensed cyclic compound represented by Formula 1 (seeFormula 1′ below) is linked to ring A₅ via “N”, and “Ring B” is linkedto a carbon atom of ring A₅, which is linked to “N” of “Ring A”, in anortho-position. In this regard, a conjugation length of the condensedcyclic compound represented by Formula 1 shortens, and thus thecondensed cyclic compound represented by Formula 1 can have a hightriplet energy level. As a result, while not wishing to be bound bytheory, it is believed that the condensed cyclic compound represented byFormula 1 may have a triplet (T₁) energy level suitable for anelectronic device, for example, a material of an organic light-emittingdevice (for example, a material for a host of an emission layer).

X₂ of “Ring B” in Formula 1 is O or S, and the condensed cyclic compoundrepresented by Formula 1 includes 1, 2, 3 or 4 cyano groups as asubstituent. Thus, electric characteristics (for example, HOMO, LUMOenergy level, etc.) of the condensed cyclic compound represented byFormula 1 may be easily controlled to improve electric charge (forexample, electron) mobility. The condensed cyclic compound representedby Formula 1 has 1, 2, 3 or 4 cyano groups as a substituent and thus,has an excellent heat resistance. As a result, the condensed cycliccompound represented by Formula 1 can have a HOMO/LUMO energy levelsuitable for an electronic device, for example, a material for anorganic light-emitting device (for example, a material for a host of anemission layer, and a common layer), and can have a long lifespan.

For example, HOMO, LUMO, T₁ and S₁ energy levels of Compounds 3, 4, 9,16, 28, 408, 409, 413, 415, 421, 423, 424, 429, 437, 450, 459, B and Cmay be structurally optimized at a level of B3LYP/6-31G(d,p) by using adensity functional theory (DFT) method of a Gaussian program andevaluated by simulation. The results thereof are shown in Table 1 below:

TABLE 1 Compound No. HOMO (eV) LUMO (eV) T₁ (eV) S₁ (eV) Compound 3−5.624 −1.798 2.964 3.194 Compound 4 −5.544 −1.636 3.096 3.202 Compound9 −5.483 −1.433 3.126 3.529 Compound 16 −5.669 −1.793 3.079 3.176Compound 28 −5.560 −1.657 3.048 3.202 Compound 408 −5.920 −1.606 3.1193.900 Compound 409 −5.958 −1.903 3.119 3.393 Compound 413 −5.491 −1.6852.950 3.121 Compound 415 −5.490 −1.873 2.921 2.989 Compound 421 −5.429−1.694 3.000 3.172 Compound 423 −5.463 −1.837 2.912 3.060 Compound 424−5.378 −1.681 3.004 3.065 Compound 429 −5.441 −1.827 2.943 2.995Compound 437 −5.426 −1.694 2.969 3.100 Compound 450 −5.494 −1.569 2.9513.245 Compound 459 −5.472 −1.714 2.988 3.082 Compound B −5.175 −1.2782.599 3.351 Compound C −5.543 −1.811 2.912 3.271

A method of synthesizing the condensed cyclic compound represented byFormula 1 may be understood by one of ordinary skill in the art byreferring to Synthesis Examples described below.

In this regard, the condensed cyclic compound represented by Formula 1may be suitable to be used as a material for an organic layer of anorganic light-emitting device, for example, a host for an emission layerin the organic layer. According to another aspect, the organiclight-emitting device may include:

-   -   a first electrode;    -   a second electrode; and    -   an organic layer disposed between the first electrode and the        second electrode,    -   wherein the organic layer includes the emission layer and at        least one condensed cyclic compound represented by Formula 1.

The organic light-emitting device includes the organic layer includingthe condensed cyclic compound represented by Formula 1, thereby havinglow driving voltage, high efficiency and long lifespan.

The condensed cyclic compound represented by Formula 1 may be usedbetween a pair of electrodes in an organic light-emitting device. Forexample, the condensed cyclic compound may be included in at least oneselected from:

-   -   i) an emission layer,    -   ii) a hole transport region disposed between a first electrode        and an emission layer (for example, at least one selected from a        hole injection layer, a hole transport layer, and an electron        blocking layer is included in the hole transport region), and    -   iii) an electron transport region disposed between an emission        layer and a second electrode (for example, at least one selected        from a hole blocking layer, an electron transport layer, and an        electron injection layer is included in the electron transport        region).

For example, the condensed cyclic compound represented by Formula 1 maybe included in the emission layer. Here, the condensed cyclic compoundincluded in the emission layer may serve as a host, and the emissionlayer may further include a dopant (a fluorescent dopant, aphosphorescent dopant or a delayed fluorescent dopant). The emissionlayer may be a red emission layer, a green emission layer, or a blueemission layer respectively emitting red light, green light or bluelight. According to an embodiment, the condensed cyclic compoundrepresented by Formula 1 may be included in the emission layer, theemission layer may further include a phosphorescent dopant, and theemission layer may emit blue light.

The expression as used herein “(an organic layer) includes at least onecondensed cyclic compound” may be understood as “(organic layer) mayinclude one condensed cyclic compound represented by Formula 1 or two ormore different condensed cyclic compounds represented by Formula 1”.

For example, the organic layer may include only Compound 1 as thecondensed cyclic compound. In this regard, Compound 1 may be included inthe emission layer of the organic light-emitting device. Alternatively,the organic layer may include Compound 1 and Compound 2 as the condensedcyclic compounds. In this regard, Compound 1 and Compound 2 may beincluded in the same layer (for example, both Compound 1 and Compound 2may be included in the emission layer), or in different layers.

The first electrode may be anode, which is a hole injection electrode,and the second electrode may be a cathode, which is an electroninjection electrode. Alternatively, the first electrode may be acathode, which is an electron injection electrode, and the secondelectrode may be an anode, which is a hole injection electrode.

For example, the first electrode may be an anode, the second electrodemay be a cathode, and the organic layer may include a hole transportregion disposed between the first electrode and the emission layer andan electron transport region disposed between the emission layer and thesecond electrode, wherein the hole transport region includes at leastone selected from a hole injection layer, a hole transport layer and anelectron blocking layer, and the electron transport region includes atleast one selected from a hole blocking layer, an electron transportlayer and an electron injection layer.

As used herein, the term the “organic layer” refers to a single and/or aplurality of layers disposed between the first electrode and the secondelectrode in an organic light-emitting device. The “organic layer” mayinclude not only organic compounds but also organometallic complexesincluding metals.

FIG. is a schematic view of an organic light-emitting device 10according to an embodiment. Hereinafter, a structure and a method ofmanufacturing the organic light-emitting device according to anembodiment will be described with reference to FIG. The organiclight-emitting device 10 includes a first electrode 11, an organic layer15, and a second electrode 19, which are sequentially layered in thestated order.

A substrate may be additionally disposed under the first electrode 11 oron the second electrode 19. The substrate may be a conventionalsubstrate that is used in an organic light-emitting device, such asglass substrate or a transparent plastic substrate, each havingexcellent mechanical strength, thermal stability, transparency, surfacesmoothness, ease of handling, and water repellency.

The first electrode 11 may be formed by vacuum-depositing or sputteringa material for forming a first electrode on the substrate. The firstelectrode 11 may be an anode. The material for the first electrode 11may be selected from materials with a high work function so as tofacilitate hole injection. The first electrode 11 may be a reflectiveelectrode, a semi-transmissive electrode, or a transmissive electrode.The material for the first electrode 11 may be selected from indium tinoxide (ITO), indium zinc oxide (IZO), tin oxide (SnO₂), and zinc oxide(ZnO). Alternatively, a metal such as magnesium (Mg), aluminum (Al),aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), andmagnesium-silver (Mg—Ag) may be used herein.

The first electrode 11 may have a single layer structure or amulti-layer structure including a plurality of layers. For example, thefirst electrode 11 may have a triple-layer structure of ITO/Ag/ITO, butembodiments are not limited thereto.

The organic layer 15 is disposed on the first electrode 11.

The organic layer 15 may include a hole transport region, an emissionlayer, and an electron transport region.

The hole transport region may be disposed between the first electrode 11and the emission layer.

The hole transport region may include at least one selected from a holeinjection layer, hole transport layer, electron blocking layer, andbuffer layer.

The hole transport region may only include a hole injection layer or ahole transport layer. Alternatively, the hole transport region mayinclude a structure in which a hole injection layer/a hole transportlayer or a hole injection layer/a hole transport layer/an electronblocking layer are sequentially layered on the first electrode 11.

When the hole transport region includes a hole injection layer, the holeinjection layer may be formed on the first electrode 11 by using variousmethods such as vacuum-deposition, spin coating, casting, andLangmuir-Blodgett (LB) method.

When a hole injection layer is formed by vacuum-deposition, though theconditions may vary depending on a compound that is used as a holeinjection material and a structure and thermal properties of a desiredhole injection layer, for example, the vacuum-deposition may beperformed at a deposition temperature in a range of about 100° C. toabout 500° C., at a vacuum degree in a range of about 10⁻⁸ to about 10⁻³torr, and at a deposition rate in a range of about 0.01 Angstroms persecond (Å/sec) to about 100 Å/sec, but embodiments are not limitedthereto.

When a hole injection layer is formed by spin coating, though theconditions may vary depending on a compound that is used as a holeinjection material and a structure and thermal properties of a desiredhole injection layer, the spin coating may be performed at a coatingrate in a range of about 2,000 revolutions per minute (rpm) to about5,000 rpm, and at a temperature in a range of about 80° C. to 200° C.for removing a solvent after the spin coating, but embodiments are notlimited thereto.

The conditions for forming a hole transport layer and an electronblocking layer may be understood by referring to the conditions forforming the hole injection layer.

The hole transport region may include at least one selected fromm-MTDATA, TDATA, 2-TNATA, NPB, β-NPB, TPD, a spiro-TPD, a spiro-NPB,methylated-NPB, TAPC, HMTPD, 4,4′,4″-tris(N-carbazolyl)triphenylamine(TCTA), polyaniline/dodecylbenzene sulfonic acid (Pani/DBSA),poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS),polyaniline/camphor sulfonic acid (Pani/CSA),(polyaniline)/poly(4-styrenesulfonate) (PANI/PSS), a compoundrepresented by Formula 201 below, and a compound represented by Formula202 below:

Ar₁₀₁ and Ar₁₀₂ in Formula 201 may be each independently selected from

-   -   a phenylene group, a pentalenylene group, an indenylene group, a        naphthylene group, an azulenylene group, a heptalenylene group,        an acenaphthylene group, a fluorenylene group, a phenalenylene        group, a phenanthrenylene group, an anthracenylene group, a        fluoranthenylene group, a triphenylenylene group, a pyrenylene        group, a chrysenylenylene group, a naphthacenylene group, a        picenylene group, a perylenylene group and a pentacenylene        group; and    -   a phenylene group, a pentalenylene group, an indenylene group, a        naphthylene group, an azulenylene group, a heptalenylene group,        an acenaphthylene group, a fluorenylene group, a phenalenylene        group, a phenanthrenylene group, an anthracenylene group, a        fluoranthenylene group, a triphenylenylene group, a pyrenylene        group, a chrysenylenylene group, a naphthacenylene group, a        picenylene group, a perylenylene group and a pentacenylene        group, each substituted with at least one selected from a        deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a        nitro group, an amino group, an amidino group, a hydrazine        group, a hydrazone group, a carboxylic acid group or a salt        thereof, a sulfonic acid group or a salt thereof, a phosphoric        acid group or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀        alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a        C₃-C₁₀ cycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀        heterocycloalkyl group, a C₁-C₁₀ heterocycloalkenyl group, a        C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio        group, a C₇-C₆₀ arylalkyl group, a C₁-C₆₀ heteroaryl group, a        C₁-C₆₀ heteroaryloxy group, a C₁-C₆₀ heteroarylthio group, a        C₂-C₆₀ heteroarylalkyl group, a monovalent non-aromatic        condensed polycyclic group and a monovalent non-aromatic        condensed heteropolycyclic group.

xa and xb in Formula 201 may each independently be an integer of 0 to 5,or may be 0, 1 or 2. For example, xa may be 1 and xb may be 0, butembodiments are not limited thereto.

R₁₀₁ to R₁₀₈, R₁₁₁ to R₁₁₉ and R₁₂₁ to R₁₂₄ in Formulae 201 and 202 maybe each independently selected from

-   -   a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a        cyano group, a nitro group, an amino group, an amidino group, a        hydrazine group, a hydrazone group, a carboxylic acid group or a        salt thereof, a sulfonic acid group or a salt thereof, a        phosphoric acid group or a salt thereof, a C₁-C₁₀ alkyl group        (for example, a methyl group, an ethyl group, a propyl group, a        butyl group, pentyl group, a hexyl group, etc.) and a C₁-C₁₀        alkoxy group (for example, a methoxy group, an ethoxy group, a        propoxy group, butoxy group, a pentoxy group, etc.);    -   a C₁-C₁₀ alkyl group and a C₁-C₁₀ alkoxy group, each substituted        with at least one selected from a deuterium, —F, —Cl, —Br, —I, a        hydroxyl group, a cyano group, a nitro group, an amino group, an        amidino group, a hydrazine group, a hydrazone group, a        carboxylic acid group or a salt thereof, a sulfonic acid group        or a salt thereof and a phosphoric acid group or a salt thereof;    -   a phenyl group, a naphthyl group, an anthracenyl group, a        fluorenyl group and a pyrenyl group; and    -   a phenyl group, a naphthyl group, an anthracenyl group, a        fluorenyl group and a pyrenyl group, each substituted with at        least one selected from a deuterium, —F, —Cl, —Br, —I, a        hydroxyl group, a cyano group, a nitro group, an amino group, an        amidino group, a hydrazine group, a hydrazone group, a        carboxylic acid group or a salt thereof, a sulfonic acid group        or a salt thereof, a phosphoric acid group or a salt thereof, a        C₁-C₁₀ alkyl group and a C₁-C₁₀ alkoxy group,    -   but embodiments are not limited thereto.

R₁₀₉ in Formula 201 may be selected from

-   -   a phenyl group, a naphthyl group, an anthracenyl group and a        pyridinyl group; and    -   a phenyl group, a naphthyl group, an anthracenyl group and a        pyridinyl group, each substituted with at least one selected        from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano        group, a nitro group, an amino group, an amidino group, a        hydrazine group, a hydrazone group, a carboxylic acid group or a        salt thereof, a sulfonic acid group or a salt thereof, a        phosphoric acid group or a salt thereof, a C₁-C₂₀ alkyl group, a        C₁-C₂₀ alkoxy group, a phenyl group, a naphthyl group, an        anthracenyl group and a pyridinyl group.

According to an embodiment, the compound represented by Formula 201 maybe represented by Formula 201A, but embodiments are not limited thereto:

Descriptions of R₁₀₁, R₁₁₁, R₁₁₂ and R₁₀₉ in Formula 201A are the sameas described herein.

For example, the compound represented by Formula 201 and the compoundrepresented by Formula 202 may include Compounds HT1 to HT20, butembodiments are not limited thereto:

A thickness of the hole transport region may be in a range of about 100Angstroms (Å) to about 10,000 Å, for example, about 100 Å to about 1,000Å. When the hole transport region includes at least one of a holeinjection layer and a hole transport layer, the thickness of the holeinjection layer may be in a range of about 100 Å to about 10,000 Å, andfor example, about 100 Å to about 1,000 Å, and the thickness of the holetransport layer may be in a range of about 50 Å to about 2,000 Å, andfor example, about 100 Å to about 1,500 Å. While not wishing to be boundby theory, it is understood that when the thicknesses of the holetransport region, the hole injection layer, and the hole transport layerare within these ranges, excellent hole transport characteristics may beobtained without a substantial increase in driving voltage.

The hole transport region may further include, in addition to thementioned materials above, a charge-generating material to improveconductive properties. The charge-generating material may behomogeneously or non-homogeneously dispersed throughout the holetransport region.

The charge-generating material may be, for example, a p-dopant. Thep-dopant may be one selected from a quinone derivative, a metal oxide,and a cyano group-containing compound, but embodiments are not limitedthereto. For example, non-limiting examples of the p-dopant are aquinone derivative, such as tetracyanoquinonedimethane (TCNQ) or2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinonedimethane (F4-TCNQ); ametal oxide, such as a tungsten oxide or a molybdenum oxide; and acompound containing a cyano group, such as Compound HT-D1 and HP-1, butembodiments are not limited thereto.

The hole transport region may further include a buffer layer.

The buffer layer may compensate for an optical resonance distanceaccording to a wavelength of light emitted from the emission layer toimprove the efficiency of an organic light-emitting device.

An emission layer may be formed on the hole transport region by usingvarious methods, such as vacuum-deposition, spin coating, casting, or anLB method. When the emission layer is formed by vacuum-deposition orspin coating, vacuum-deposition and coating conditions for the emissionlayer may be generally similar to the conditions for forming a holeinjection layer, though the conditions may vary depending on thecompound used.

The hole transport region may further include an electron blockinglayer. The electron blocking layer may include a known material, forexample, mCP, but embodiments are not limited thereto.

When the organic light-emitting device is a full color organiclight-emitting device, the emission layer may be patterned into a redemission layer, a green emission layer, and a blue emission layer.Alternatively, the emission layer may have a structure in which the redemission layer, the green emission layer, and/or the blue emission layerare layered to emit white light or other various embodiments arepossible.

The emission layer may include the condensed cyclic compound representedby Formula 1. For example, the emission layer may include a host and adopant, and the host may include the condensed cyclic compoundrepresented by Formula 1.

A dopant in the emission layer may include at least one selected from afluorescent dopant emitting light according to fluorescence emissionmechanism, a phosphorescent dopant emitting light according tophosphorescence emission mechanism, and a delayed fluorescent dopantemitting light according to thermally activated delayed fluorescenceemission mechanism.

According to an embodiment, a dopant in the emission layer may be aphosphorescent dopant, and the phosphorescent dopant may include anorganometallic compound represented by Formula 81:

In Formula 81,

-   -   M may be selected from iridium (Ir), platinum (Pt), osmium (Os),        titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu),        terbium (Tb) and thulium (Tm),    -   Y₁ to Y₄ may each independently be carbon (C) or nitrogen (N),    -   Y₁ and Y₂ may be linked to each other by a single bond or a        double bond, and Y₃ and Y₄ may be linked to each other by a        single bond or a double bond,    -   CY₁ and CY₂ may each independently be a benzene, a naphthalene,        a fluorene, a spiro-bifluorene, an indene, a pyrrole, a        thiophene, a furan, an imidazole, a pyrazole, a thiazole, an        isothiazole, an oxazole, an isooxazole, a pyridine, a pyrazine,        a pyrimidine, a pyridazine, a quinoline, an isoquinoline, a        benzoquinoline, a quinoxaline, a quinazoline, a carbazole, a        benzoimidazole, a benzofuran, a benzothiophene, an        isobenzothiophene, a benzoxazole, an isobenzoxazole, a triazole,        a tetrazole, an oxadiazole, a triazine, a dibenzofuran or a        dibenzothiophene, and CY₁ and CY₂ may be optionally further        linked to each other by an organic linking group,    -   R₈₁ and R₈₂ may be each independently selected from a hydrogen,        a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group,        a nitro group, an amino group, an amidino group, a hydrazine        group, a hydrazone group, a carboxylic acid group or a salt        thereof, a sulfonic acid group or a salt thereof, a phosphoric        acid group or a salt thereof, —SF₅, a substituted or        unsubstituted C₁-C₆₀ alkyl group, a substituted or unsubstituted        C₂-C₆₀ alkenyl group, a substituted or unsubstituted C₂-C₆₀        alkynyl group, a substituted or unsubstituted C₁-C₆₀ alkoxy        group, a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, a        substituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, a        substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a        substituted or unsubstituted C₁-C₁₀ heterocycloalkenyl group, a        substituted or unsubstituted C₆-C₆₀ aryl group, a substituted or        unsubstituted C₆-C₆₀ aryloxy group, a substituted or        unsubstituted C₆-C₆₀ arylthio group, a substituted or        unsubstituted C₇-C₆₀ arylalkyl group, a substituted or        unsubstituted C₁-C₆₀ heteroaryl group, a substituted or        unsubstituted C₁-C₆₀ heteroaryloxy group, a substituted or        unsubstituted C₁-C₆₀ heteroarylthio group, a substituted or        unsubstituted C₂-C₆₀ heteroarylalkyl group, a substituted or        unsubstituted monovalent non-aromatic condensed polycyclic        group, a substituted or unsubstituted monovalent non-aromatic        condensed heteropolycyclic group, —N(Q₁)(Q₂), —Si(Q₃)(Q₄)(Q₅)        and —B(Q₆)(Q₇),    -   a81 and a82 may each independently be an integer of 1 to 5,    -   n81 may be integer of 0 to 4,    -   n82 may be 1, 2 or 3, and    -   L₈₁ may be a monovalent organic ligand, a divalent organic        ligand or a trivalent organic ligand. Q₁ to Q₇ may have the same        definitions as Q₁ to Q₃ in —Si(Q₁)(Q₂)(Q₃) in Formula 1.

Descriptions of R₈₁ and R₈₂ may be the same as the description of R₁₁provided herein.

The phosphorescent dopant may include at least one selected fromCompounds PD1 to PD78, FIr6 and PtOEP, but embodiments are not limitedthereto:

In some embodiments, the phosphorescent dopant may include PtOEP:

When the emission layer includes a host and a dopant, an amount of thedopant may be selected from a range of about 0.01 part by weight toabout 20 parts by weight based on about 100 parts by weight of the host,but embodiments are not limited thereto.

A thickness of the emission layer may be in a range of about 100 Å toabout 1000 Å, for example, about 200 Å to about 600 Å. While not wishingto be bound by theory, it is understood that when the thickness of theemission layer is within this range, excellent light-emissioncharacteristics may be obtained without a substantial increase indriving voltage.

Then, an electron transport region may be disposed on the emissionlayer.

The electron transport region may include at least one selected from ahole blocking layer, an electron transport layer, and an electroninjection layer, but is not limited thereto.

For example, the electron transport region may have a structure of ahole blocking layer/an electron transport layer/an electron injectionlayer or an electron transport layer/an electron injection layer, but itis not limited thereto. The electron transport layer may have a singlelayer structure or a multi-layer structure including two or moredifferent materials.

The conditions for forming a hole blocking layer, an electron transportlayer, and an electron injection layer may be understood by referring tothe conditions for forming the hole injection layer.

When the electron transport region includes a hole blocking layer, thehole blocking layer may, for example, include at least one of BCP, Bphenand TmPyPB, but is not limited thereto.

A thickness of the hole blocking layer may be in a range of about 20 Åto about 1,000 Å, for example, about 30 Å to about 300 Å. While notwishing to be bound by theory, it is understood that when the thicknessof the hole blocking layer is within this range, excellent hole blockingcharacteristics may be obtained without a substantial increase indriving voltage.

The electron transport layer may include at least one selected from BCP,BPhen Alq3, BAlq, TAZ, and NTAZ.

In some embodiments, the electron transport layer may include at leastone selected from Compounds ET1 and ET2, but it is not limited thereto.

A thickness of the electron transport layer may be in a range of about100 Å to about 1,000 Å, for example, about 150 Å to about 500 Å. Whilenot wishing to be bound by theory, it is understood that when thethickness of the electron transport layer is within this range,excellent electron transport characteristics may be obtained without asubstantial increase in driving voltage.

The electron transport layer may further include a metal-containingmaterial in addition to the materials described above.

The metal-containing material may include a Li complex. The Li complexmay include, for example, Compound ET-D1 (lithium quinolate, LiQ) orET-D2.

The electron transport region may include an electron injection layer(EIL) that facilitates electron injection from the second electrode 19.

The electron injection layer may include at least one selected from,LiF, NaCl, CsF, Li₂O, and BaO.

A thickness of the electron injection layer may be in a range of about 1Å to about 100 Å, for example, about 3 Å to about 90 Å. While notwishing to be bound by theory, it is understood that when the thicknessof the electron injection layer is within this range, excellent electroninjection characteristics may be obtained without a substantial increasein driving voltage.

The second electrode 19 is disposed on the organic layer 15. The secondelectrode 19 may be a cathode. A material for the second electrode 19may be a material having a relatively low work function, such as ametal, an alloy, an electrically conductive compound, and a mixturethereof. Detailed examples of the material for forming the secondelectrode 19 are lithium (Li), magnesium (Mg), aluminum (Al),aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), andmagnesium-silver (Mg—Ag). Alternatively, ITO or IZO may be used to forma transmissive second electrode 19 to manufacture a top emissionlight-emitting device, and such a variation may be possible.

Hereinbefore, an organic light-emitting device has been described withreference to FIG., but embodiments are not limited thereto.

A C₁-C₆₀ alkyl group as used herein refers to a linear or branchedaliphatic saturated hydrocarbon monovalent group having 1 to 60 carbonatoms. Detailed examples thereof are a methyl group, an ethyl group, apropyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group,a pentyl group, an iso-amyl group, and a hexyl group. A C₁-C₆₀ alkylenegroup as used herein refers to a divalent group having the samestructure as a C₁-C₆₀ alkyl group.

A C₁-C₆₀ alkoxy group as used herein refers to a monovalent grouprepresented by -OA₁₀₁ (wherein A₁₀₁ is the C₁-C₆₀ alkyl group). Detailedexamples thereof are a methoxy group, an ethoxy group, and anisopropyloxy group.

A C₂-C₆₀ alkenyl group as used herein refers to a group formed byplacing at least one carbon-carbon double bond in the middle or at theterminal of the C₂-C₆₀ alkyl group. Detailed examples thereof are anethenyl group, a propenyl group, and a butenyl group. A C₂-C₆₀alkenylene group as used herein refers to a divalent group having thesame structure as a C₂-C₆₀ alkenyl group.

A C₂-C₆₀ alkynyl group as used herein refers to a group formed bysubstituting at least one carbon triple bond in the middle or at theterminal of the C₂-C₆₀ alkyl group. Detailed examples thereof are anethynyl group and a propynyl group. A C₂-C₆₀ alkynylene group as usedherein refers to a divalent group having the same structure as a C₂-C₆₀alkynyl group.

A C₃-C₁₀ cycloalkyl group as used herein refers to a monovalentmonocyclic saturated hydrocarbon group including 3 to 10 carbon atoms.Detailed examples thereof are a cyclopropyl group, a cyclobutyl group, acyclopentyl group, a cyclohexyl group, and a cycloheptyl group. A C₃-C₁₀cycloalkylene group as used herein refers to a divalent group having thesame structure as a C₃-C₁₀ cycloalkyl group.

A C₁-C₁₀ heterocycloalkyl group as used herein refers to a monovalentsaturated monocyclic group including at least one hetero atom selectedfrom N, O, P, Si and S as a ring-forming atom and 1 to 10 carbon atoms.Detailed examples thereof are a tetrahydrofuranyl group and atetrahydrothiophenyl group. A C₁-C₁₀ heterocycloalkylene group as usedherein refers to a divalent group having the same structure as a C₁-C₁₀heterocycloalkyl group.

A C₃-C₁₀ cycloalkenyl group as used herein refers to a monovalentmonocyclic group that has 3 to 10 carbon atoms and at least one doublebond in its ring, and which is not aromatic. Detailed examples thereofare a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenylgroup. A C₃-C₁₀ cycloalkenylene group as used herein refers to adivalent group having the same structure as a C₃-C₁₀ cycloalkenyl group.

A C₁-C₁₀ heterocycloalkenyl group as used herein refers to a monovalentmonocyclic group including at least one hetero atom selected from N, O,P, Si and S as a ring-forming atom, 1 to 10 carbon atoms, and at leastone double bond in its ring. Detailed examples of the C₁-C₁₀heterocycloalkenyl group are a 2,3-dihydrofuranyl group and a2,3-dihydrothiophenyl group. A C₂-C₁₀ heterocycloalkenylene group asused herein refers to a divalent group having the same structure as aC₁-C₁₀ heterocycloalkenyl group.

A C₆-C₆₀ aryl group as used herein refers to a monovalent group having acarbocyclic aromatic system having 6 to 60 carbon atoms, and a C₆₀-C₆₀arylene group as used herein refers to a divalent group having acarbocyclic aromatic system having 6 to 60 carbon atoms. Detailedexamples of the C₆-C₆₀ aryl group are a phenyl group, a naphthyl group,an anthracenyl group, a phenanthrenyl group, a pyrenyl group, and achrysenyl group. When the C₆-C₆₀ aryl group and the C₆-C₆₀ arylene groupeach include two or more rings, the rings may be fused to each other.

A C₁-C₆₀ heteroaryl group as used herein refers to a monovalent grouphaving a heterocyclic aromatic system including at least one hetero atomselected from N, O, P, Si and S as a ring-forming atom and 1 to 60carbon atoms. A C₁-C₆₀ heteroarylene group as used herein refers to adivalent group having a carbocyclic aromatic system including at leastone hetero atom selected from N, O, P, Si and S as a ring-forming atomand 1 to 60 carbon atoms. Detailed examples of the C₁-C₆₀ heteroarylgroup include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group,a pyridazinyl group, a triazinyl group, a quinolinyl group, and anisoquinolinyl group. When the C₁-C₆₀ heteroaryl group and the C₁-C₆₀heteroarylene group each include a plurality of rings, the rings may befused to each other.

A C₆-C₆₀ aryloxy group as used herein indicates -OA₁₀₂ (wherein A₁₀₂ isthe C₆-C₆₀ aryl group), and a C₆-C₆₀ arylthio group as used hereinindicates -SA₁₀₃ (wherein A₁₀₃ is the C₆-C₆₀ aryl group), and a C₇-C₆₀arylalkyl group as used herein indicates -A₁₀₄A₁₀₅ (wherein A₁₀₄ is theC₆-C₆₀ aryl group and A₁₀₅ is the C₁-C₆₀ alkyl group).

A C₁-C₆₀ heteroaryloxy group as used herein indicates -OA₁₀₆ (whereinA₁₀₆ is the C₁-C₆₀ heteroaryl group), a C₁-C₆₀ heteroarylthio group asused herein indicates -SA₁₀₇ (wherein A₁₀₇ is the C₁-C₆₀ heteroarylgroup), and a C₁-C₆₀ heteroarylalkyl group as used herein indicates-A₁₀₈A₁₀₉ (wherein A₁₀₉ is the C₁-C₆₀ heteroaryl group and A₁₀₈ is theC₁-C₆₀ alkyl group).

A monovalent non-aromatic condensed polycyclic group as used hereinrefers to a monovalent group that has two or more rings condensed toeach other, only carbon atoms (for example, the number of carbon atomsmay be in a range of 8 to 60) as ring forming atoms, wherein themolecular structure as a whole is non-aromatic in the entire molecularstructure. Detailed examples of the non-aromatic condensed polycyclicgroup include a fluorenyl group. A divalent non-aromatic condensedpolycyclic group as used herein refers to a divalent group having thesame structure as the monovalent non-aromatic condensed polycyclicgroup.

A monovalent non-aromatic condensed heteropolycyclic group as usedherein refers to a monovalent group that has a plurality of ringscondensed with each other, has a hetero atom selected from N, O, P, Siand S, other than carbon atoms (for example, the number of carbon atomsmay be in a range of 1 to 60), as ring-forming atoms, wherein themolecular structure as a whole is non-aromatic in the entire molecularstructure. The monovalent non-aromatic condensed heteropolycyclic groupincludes a carbazolyl group. A divalent non-aromatic condensedhetero-polycyclic group as used herein refers to a divalent group havingthe same structure as the monovalent non-aromatic condensedhetero-polycyclic group.

At least one substituent of the substituted C₃-C₁₀ cycloalkylene group,substituted C₁-C₁₀ heterocycloalkylene group, substituted C₃-C₁₀cycloalkenylene group, substituted C₁-C₁₀ heterocycloalkenylene group,substituted C₆-C₆₀ arylene group, substituted C₁-C₆₀ heteroarylenegroup, substituted divalent non-aromatic condensed polycyclic group,substituted divalent non-aromatic condensed heteropolycyclic group,substituted C₁-C₆₀ alkyl group, substituted C₂-C₆₀ alkenyl group,substituted C₂-C₆₀ alkynyl group, substituted C₃-C₁₀ cycloalkyl group,substituted C₁-C₁₀ heterocycloalkyl group, substituted C₃-C₁₀cycloalkenyl group, substituted C₁-C₁₀ heterocycloalkenyl group,substituted C₆-C₆₀ aryl group, substituted C₆-C₆₀ aryloxy group,substituted C₆-C₆₀ arylthio group, substituted C₇-C₆₀ arylalkyl group,substituted C₁-C₆₀ heteroaryl group, substituted monovalent non-aromaticcondensed polycyclic group and substituted monovalent non-aromaticcondensed heteropolycyclic group may be selected from

-   -   a deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H,        —CFH₂, a hydroxyl group, a cyano group, a nitro group, an amino        group, an amidino group, a hydrazine group, a hydrazone group, a        carboxylic acid group or a salt thereof, a sulfonic acid group        or a salt thereof, a phosphoric acid group or a salt thereof, a        C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl        group and a C₁-C₆₀ alkoxy group;    -   a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl        group and a C₁-C₆₀ alkoxy group, each substituted with at least        one selected from a deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H,        —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a        nitro group, an amino group, an amidino group, a hydrazine        group, a hydrazone group, a carboxylic acid group or a salt        thereof, a sulfonic acid group or a salt thereof, a phosphoric        acid group or a salt thereof, a C₃-C₁₀ cycloalkyl group, a        C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a        C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀        aryloxy group, a C₆-C₆₀ arylthio group, a C₇-C₆₀ arylalkyl        group, a C₁-C₆₀ heteroaryl group, a monovalent non-aromatic        condensed polycyclic group, a monovalent non-aromatic condensed        heteropolycyclic group, —Si(Q₁₁)(Q₁₂)(Q₁₃), —N(Q₁₄)(Q₁₅) and        —B(Q₁₆)(Q₁₇);    -   a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a        C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a        C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio        group, a C₇-C₆₀ arylalkyl group, a C₁-C₆₀ heteroaryl group, a        monovalent non-aromatic condensed polycyclic group and a        monovalent non-aromatic condensed heteropolycyclic group;    -   a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a        C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a        C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio        group, a C₇-C₆₀ arylalkyl group, a C₁-C₆₀ heteroaryl group, a        monovalent non-aromatic condensed polycyclic group and a        monovalent non-aromatic condensed heteropolycyclic group, each        substituted with at least one selected from a deuterium, —F,        —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl        group, a cyano group, a nitro group, an amino group, an amidino        group, a hydrazine group, a hydrazone group, a carboxylic acid        group or a salt thereof, a sulfonic acid group or a salt        thereof, a phosphoric acid group or a salt thereof, a C₁-C₆₀        alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a        C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀        heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀        heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy        group, a C₆-C₆₀ arylthio group, a C₇-C₆₀ arylalkyl group, a        C₁-C₆₀ heteroaryl group, a monovalent non-aromatic condensed        polycyclic group, a monovalent non-aromatic condensed        heteropolycyclic group, —Si(Q₂₁)(Q₂₂)(Q₂₃), —N(Q₂₄)(Q₂₅) and        —B(Q₂₆)(Q₂₇); and    -   —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₄)(Q₃₅) and —B(Q₃₆)(Q₃₇),    -   wherein Q₁₁ to Q₁₇, Q₂₁ to Q₂₇ and Q₃₁ to Q₃₇ may be each        independently selected from a hydrogen, a deuterium, —F, —Cl,        —Br, —I, a hydroxyl group, a cyano group, a nitro group, an        amino group, an amidino group, a hydrazine group, a hydrazone        group, a carboxylic acid group or a salt thereof, a sulfonic        acid group or a salt thereof, a phosphoric acid group or a salt        thereof, a substituted or unsubstituted C₁-C₆₀ alkyl group, a        substituted or unsubstituted C₂-C₆₀ alkenyl group, a substituted        or unsubstituted C₂-C₆₀ alkynyl group, a substituted or        unsubstituted C₁-C₆₀ alkoxy group, a substituted or        unsubstituted C₃-C₁₀ cycloalkyl group, a substituted or        unsubstituted C₁-C₁₀ heterocycloalkyl group, a substituted or        unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted or        unsubstituted C₁-C₁₀ heterocycloalkenyl group, a substituted or        unsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted        C₆-C₆₀ aryloxy group, a substituted or unsubstituted C₆-C₆₀        arylthio group, a substituted or unsubstituted C₇-C₆₀ arylalkyl        group, a substituted or unsubstituted C₁-C₆₀ heteroaryl group, a        substituted or unsubstituted monovalent non-aromatic condensed        polycyclic group and a substituted or unsubstituted monovalent        non-aromatic condensed heteropolycyclic group.

When a group containing a specified number of carbon atoms issubstituted with any of the groups listed in the preceding paragraph,the number of carbon atoms in the resulting “substituted” group isdefined as the sum of the carbon atoms contained in the original(unsubstituted) group and the carbon atoms (if any) contained in thesubstituent. For example, when the term “substituted C₁-C₃₀ alkyl”refers to a C₁-C₃₀ alkyl group substituted with C₆-C₆₀ aryl group, thetotal number of carbon atoms in the resulting aryl substituted alkylgroup is C₇-C₉₀.

The term “a biphenyl group” as used herein refers to a monovalent groupin which two benzenes are linked to each other by a single bond.

The term “a terphenyl group” as used herein refers to a monovalent groupin which three benzenes are linked to each other by a single bond.

Hereinafter, a compound and an organic light-emitting device accordingto an embodiment will be described in detail with reference to SynthesisExamples and Examples, however, the present inventive concept is notlimited thereto. The expression “B was used instead of A” used indescribing Synthesis Examples means that an amount of B used wasidentical to an amount of A used based on molar equivalence.

EXAMPLE Synthesis Example 1: Synthesis of Compound 3

Compound 3 was synthesized according to the reaction scheme below.

Synthesis of Intermediate (1)

10 grams (g) (47.2 millimoles (mmol)) of dibenzofuran-2-yl boronic acid,9.43 g (47.2 mmol) of 4-bromo-3-fluorobenzonitrile, 10.9 g (9.4 mmol) ofpalladium tetrakis(triphenylphosphine) Pd(PPh₃)₄, and 19.6 g (141.5mmol) of potassium carbonate (K₂CO₃) were added to 100 milliliters (ml)of tetrahydrofuran and 70 ml of distilled water, and the resultingmixture was heated and then refluxed. When the reaction was completed,the result was cooled to room temperature, and the organic layer wasextracted with ethyl acetate, dried with anhydrous sodium sulfate(Na₂SO₄) and then concentrated. The product was separated by silica gelcolumn chromatography (dichloromethane/hexane). A solid obtained fromthe above step was recrystallized (dichloromethane/methanol) tosynthesize a white solid of Intermediate (1) (11.9 g, 41.4 mmol, yield88%).

LC-Mass (calculated: 287.29 g/mol, found: [M+1]=288 g/mol)

Synthesis of Compound 3

20 ml of N,N-dimethylformamide was slowly added to 1.9 g (47.8 mmol) ofsodium hydride (NaH) (60% in mineral oil) at 0° C., and the resultingmixture was stirred for 10 minutes. Then, 8 g (47.8 mmol) of carbazolewas melted to 30 ml of N,N-dimethylformamide, and the resulting mixturewas slowly added to the above reaction solution and stirred for 2 hoursat room temperature. A mixture of 90 ml of N,N-dimethylformamide and10.9 g (38.0 mmol) of Intermediate (1) was added to the above reactionsolution. The resulting mixture was heated to 120° C. and refluxed. Whenthe reaction was completed, the reaction solution was added tomethanol/water to obtain a precipitate, and the precipitate wasfiltered, and washed with methanol. The result obtained from the abovestep was melted in hot toluene and filtered by silica gel to obtain afiltrate. The filtrate was concentrated to obtain a solid, and the solidwas recrystallized (dichloromethane/methanol, ethyl acetate) twice tosynthesize Compound 3 (8.9 g, 20.5 mmol, yield 54%).

MALDI-TOF Mass (calculated: 434.49 g/mol, found: 434.10 g/mol)

Synthesis Example 2: Synthesis of Compound 4

Compound 4 was synthesized in the same manner as in Synthesis Example 1,except that in synthesizing Intermediate (1),3-bromo-2-fluorobenzonitrile was used instead of4-bromo-3-fluorobenzonitrile (yield 52%).

MALDI-TOF Mass (calculated: 434.49 g/mol, found: 434.15 g/mol)

Synthesis Example 3: Synthesis of Compound 28

Compound 28 was synthesized in the same manner as in Synthesis Example1, except that in synthesizing Intermediate (1),3-bromo-2-fluorobenzonitrile was used instead of4-bromo-3-fluorobenzonitrile, and dibenzothiophen-2-yl boronic acid wasused instead of dibenzofuran-2-yl boronic acid (yield 47%).

MALDI-TOF Mass (calculated: 405.55 g/mol, found: 405.11 g/mol)

Synthesis Example 4: Synthesis of Compound 409

Compound 409 was synthesized in the same manner as in Synthesis Example1, except that i) in synthesizing Intermediate (1),3-bromo-2-fluorobenzonitrile was used instead of4-bromo-3-fluorobenzonitrile, and ii) in synthesizing Compound 3,9H-carbazole-3-carbonitrile was used instead of carbazole (yield 35%).

MALDI-TOF Mass (calculated: 459.50 g/mol, found: 459.18 g/mol)

Synthesis Example 5: Synthesis of Compound 413 Synthesis of Intermediate(2)

3 g (24.6 mmol) of phenylboronic acid, 8.0 g (24.6 mmol) of3-bromo-2-fluoro-5-iodobenzonitrile, 2.84 g (2.46 mmol) of palladiumtetrakis(triphenylphosphine) (Pd(PPh₃)₄), and 10.2 g (73.8 mmol) ofpotassium carbonate (K₂CO₃) were added to 70 ml of tetrahydrofuran and36 ml of distilled water, and the resulting mixture was heated and thenrefluxed. When the reaction was completed, the result was cooled to roomtemperature, and an organic layer was extracted with ethyl acetate,dried with anhydrous sodium sulfate (Na₂SO₄), and concentrated toperform a separation process by silica gel column chromatography(dichloromethane/hexane), thereby synthesizing Intermediate (2) (5.8 g,21 mmol, yield 85%).

LC-Mass (calculated: 276.10 g/mol, found: [M+1]=277 g/mol)

Synthesis of Compound 413

Compound 413 was synthesized in the same manner as in Synthesis Example1, except that, in synthesizing Intermediate (1), Intermediate (2) wasused instead of 4-bromo-3-fluorobenzonitrile (yield 45%).

MALDI-TOF Mass (calculated: 510.58 g/mol, found: 510.17 g/mol)

Synthesis Example 6: Synthesis of Compound 415 Synthesis of Intermediate(2)-1

Intermediate (2)-1 was synthesized in the same manner as Intermediate(2) in Synthesis Example 5, except that, in synthesizing Intermediate(2) of Synthesis Example 5, 2-pyridineboronic acid was used instead ofphenylboronic acid.

Synthesis of Compound 415

Compound 415 was synthesized in the same manner as in Synthesis Example1, except that, in synthesizing Intermediate (1), Intermediate (2)-1 wasused instead of 4-bromo-3-fluorobenzonitrile (yield 23%).

MALDI-TOF Mass (calculated: 511.57 g/mol, found: 511.17 g/mol)

Synthesis Example 7: Synthesis of Compound 9

Compound 9 was synthesized in the same manner as in Synthesis Example 1,except that, in synthesizing Intermediate (1),8-bromodibenzo[b,d]furan-2-carbonitrile was used instead ofdibenzofuran-2-yl boronic acid, and 2-fluorophenylboronic acid was usedinstead of 4-bromo-3-fluorobenzonitrile (yield 32%).

MALDI-TOF Mass (calculated: 434.49 g/mol, found: 434.14 g/mol)

Synthesis Example 8: Synthesis of Compound 16

Compound 16 was synthesized in the same manner as in Synthesis Example1, except that, in synthesizing Intermediate (1),8-bromodibenzo[b,d]furan-2-carbonitrile was used instead ofdibenzofuran-2-yl boronic acid, and 3-cyano-2-fluorophenylboronic acidwas used instead of 4-bromo-3-fluorobenzonitrile (yield 40%).

MALDI-TOF Mass (calculated: 459.50 g/mol, found: 459.17 g/mol)

Synthesis Example 9: Synthesis of Compound 408

Compound 408 was synthesized in the same manner as in Synthesis Example1, except that, i) in synthesizing Intermediate (1),8-bromodibenzo[b,d]furan-2-carbonitrile was used instead ofdibenzofuran-2-yl boronic acid, and ii) in synthesizing Compound 3,9H-carbazole-3-carbonitrile was used instead of carbazole (yield 30%).

MALDI-TOF Mass (calculated: 459.50 g/mol, found: 459.15 g/mol)

Synthesis Example 10: Synthesis of Compound 421

Compound 421 was synthesized in the same manner as in Synthesis Example1, except that, i) in synthesizing Intermediate (1),2-bromo-3-fluorobenzonitrile was used instead of4-bromo-3-fluorobenzonitrile, and ii) in synthesizing Compound 3,Intermediate (3) was used instead of carbazole and the reactiontemperature was changed to 150° C. (yield 62%).

MALDI-TOF Mass (calculated: 524.57 g/mol, found: 524.17 g/mol)

Synthesis Example 11: Synthesis of Compound 423

Compound 423 was synthesized in the same manner as in Synthesis Example1, except that, in synthesizing Compound 3, Intermediate (3) was usedinstead of carbazole and the reaction temperature was changed to 150° C.(yield 57%).

MALDI-TOF Mass (calculated: 524.57 g/mol, found: 524.16 g/mol)

Synthesis Example 12: Synthesis of Compound 424

Compound 424 was synthesized in the same manner as in Synthesis Example1, except that, i) in synthesizing Intermediate (1),3-bromo-2-fluorobenzonitrile was used instead of4-bromo-3-fluorobenzonitrile, and ii) in synthesizing Compound 3,Intermediate (3) was used instead of carbazole and the reactiontemperature was changed to 150° C. (yield 60%).

MALDI-TOF Mass (calculated: 524.57 g/mol, found: 524.17 g/mol)

Synthesis Example 13: Synthesis of Compound 429

Compound 429 was synthesized in the same manner as in Synthesis Example1, except that, i) in synthesizing Intermediate (1),8-bromodibenzo[b,d]furan-2-carbonitrile was used instead ofdibenzofuran-2-yl boronic acid and 3-cyano-2-fluorophenylboronic acidwas used instead of 4-bromo-3-fluorobenzonitrile, and ii) insynthesizing Compound 3, Intermediate (3) was used instead of carbazoleand the reaction temperature was changed to 150° C. (yield 33%).

MALDI-TOF Mass (calculated: 549.58 g/mol, found: 549.18 g/mol)

Synthesis Example 14: Synthesis of Compound 437

Compound 437 was synthesized in the same manner as in Synthesis Example1, except that, i) in synthesizing Intermediate (1),3-bromo-2-fluorobenzonitrile was used instead of4-bromo-3-fluorobenzonitrile, and ii) in synthesizing Compound 3,Intermediate (4) was used instead of carbazole and the reactiontemperature was changed to 150° C. (yield 60%).

MALDI-TOF Mass (calculated: 540.63 g/mol, found: 540.17 g/mol)

Synthesis Example 15: Synthesis of Compound 450

Compound 450 was synthesized in the same manner as in Synthesis Example1, except that, i) in synthesizing Intermediate (1),3-bromo-2-fluorobenzonitrile was used instead of4-bromo-3-fluorobenzonitrile, and ii) in synthesizing Compound 3,Intermediate (5) was used instead of carbazole and the reactiontemperature was changed to 150° C. (yield 17%).

MALDI-TOF Mass (calculated: 524.57 g/mol, found: 524.19 g/mol)

Synthesis Example 16: Synthesis of Compound 459

Compound 459 was synthesized in the same manner as in Synthesis Example1, except that, i) in synthesizing Intermediate (1),3-bromo-2-fluorobenzonitrile was used instead of4-bromo-3-fluorobenzonitrile, and ii) in synthesizing Compound 3,Intermediate (6) was used instead of carbazole and the reactiontemperature was changed to 150° C. (yield 31%).

MALDI-TOF Mass (calculated: 524.57 g/mol, found: 524.18 g/mol)

Evaluation Example 1: Evaluation of Thermal Characteristics

Thermal analysis (N₂ atmosphere, temperature range: room temperature800° C. (10° C./min)-TGA, from room temperature to 400° C.-DSC, PanType: Pt Pan in disposable Al pan(TGA), disposable Al pan(DSC)) wasperformed on Compounds 3, 4, 413, 424 and A by using Thermo GravimetricAnalysis (TGA) and Differential Scanning Calorimetry (DSC). The resultsthereof are shown in Table 2. Table 2 shows that Compounds 3, 4, 413 and424 have an excellent thermal stability compared to Compound A.

TABLE 2 decomposition start Compound No. Tg (° C.) temperature (° C.) 389 292 4 83 285 413 106 362 424 129 393 Compound A 72 317

Example 1

A glass substrate having an indium tin oxide (ITO) electrode as a firstelectrode having a thickness of 1,500 Angstroms (Å) thereon wassonicated with distilled water and then further sonicated with solventsuch as isopropyl alcohol, acetone, and methanol and dried to be placedin a plasma cleaner. Next, the glass substrate was cleaned for 5 minutesby using oxygen plasma and then mounted on a vacuum depositionapparatus.

Compound NPB was vacuum deposited on the ITO electrode of the glasssubstrate to form a hole transport layer having a thickness of 1,200 Å,and mCP was deposited on the hole transport layer to form an electronblocking layer having a thickness of 100 Å. As a result, a holetransport region was formed.

Compound 3 (host) and Compound FIr6 (dopant, 10 percent by weight (wt%)) were co-deposited on the hole transport region to form an emissionlayer having a thickness of 300 Å.

TmPyPB was vacuum deposited on the emission layer to form a holeblocking layer having a thickness of 100 Å, and Compound Alq₃ wasdeposited on the hole blocking layer to form an electron transport layerhaving a thickness of 250 Å. Then, LiF was deposited on the electrontransport layer to form an electron injection layer having a thicknessof 5 Å, and Al second electrode (cathode) having a thickness of 1,000 Åwas formed on the electron injection layer, thereby manufacturing anorganic light-emitting device.

Examples 2 to 16 and Comparative Examples 1 to 4

Organic light-emitting devices were manufactured in the same manner asin Example 1, except that when forming an emission layer, Compounds inTable 3 were used as a host instead of Compound 3.

Evaluation Example 2: Characteristic Evaluation of OrganicLight-Emitting Device

The driving voltage, current efficiency and lifespan of each organiclight-emitting device manufactured in Examples 1 to 16 and ComparativeExamples 1 to 4 were evaluated by using a Keithley SMU 236 and aluminance meter PR650. In Table 3, the driving voltage and currentefficiency of Examples 2 to 16 and Comparative Examples 1 to 4 wererespectively expressed in a relative value compared to “100”, whichdenotes the driving voltage and current efficiency of an organiclight-emitting device in Example 1. Lifespan (T₉₅) in Table 3 refers toan amount of time (hour, hr) lapsed until luminance was decreased to 95%of its initial value, where the initial value was measured in 500 nit.Lifespan (T₉₅) of Examples 2 to 16 and Comparative Examples 1 to 4 wasexpressed in a relative value compared to “100”, which denotes lifespan(T₉₅) of an organic light-emitting device in Example 1.

TABLE 3 current driving efficiency T₉₅ voltage (V) (cd/A) (hr) (relative(relative (relative host value) value) value) Example 1 Compound 3 100100 100 Example 2 Compound 4 88 108 171 Example 3 Compound 9 70 103 50Example 4 Compound 16 77 114 58 Example 5 Compound 28 94 102 119 Example6 Compound 408 72 94 75 Example 7 Compound 409 84 115 133 Example 8Compound 413 91 110 171 Example 9 Compound 415 76 84 65 Example 10Compound 421 67 83 143 Example 11 Compound 423 66 81 72 Example 12Compound 424 63 89 105 Example 13 Compound 429 72 98 52 Example 14Compound 437 63 94 80 Example 15 Compound 450 67 103 74 Example 16Compound 459 65 79 53 Comparative Compound A 112 75 21 Example 1Comparative Compound B 109 62 27 Example 2 Comparative Compound C 87 4848 Example 3 Comparative Compound D 101 78 25 Example 4

Table 3 shows that organic light-emitting devices in Examples 1 to 16have lower or comparable driving voltage, higher efficiency and longerlifespan compared to organic light-emitting devices in ComparativeExamples 1 to 4.

It should be understood that exemplary embodiments described hereinshould be considered in a descriptive sense only and not for purposes oflimitation. Descriptions of features or aspects within each exemplaryembodiment should typically be considered as available for other similarfeatures or aspects in other exemplary embodiments.

While one or more exemplary embodiments have been described withreference to the figures, it will be understood by those of ordinaryskill in the art that various changes in form and details may be madetherein without departing from the spirit and scope of the presentdisclosure as defined by the following claims.

What is claimed is:
 1. A condensed cyclic compound represented by one ofFormula 1A to 1H:

wherein, in Formulae 1A to 1H, X₄ is selected from O, S, N(R_(4c)) andC(R_(4d))(R_(4e)), R_(4a) to R_(4e) are the same as R₄, aa4 is aninteger of 0 to 3, ab4 is an integer of 0 to 2, X₁ is selected from asingle bond, O, S, N(R₁₁) and C(R₁₂)(R₁₃), X₂ is O or S, ring A₁ to ringA₄ are each independently a C₅-C₆₀ carbocyclic group or a C₂-C₆₀heterocyclic group, ring A₃ is selected from a benzene, a pyridine, apyrimidine, a pyrazine, a pyridazine, an indene, an indole, abenzofuran, a benzothiophene, a fluorene, a carbazole, a dibenzofuranand a dibenzothiophene, ring A₅ is selected from a benzene, a pyridine,a pyrimidine, a pyrazine, a pyridazine and a triazine, ring A₆ isrepresented by Formula 2A, ring A₇ is represented by Formula 2B, R₁ toR₆ and R₁₁ to R₁₃ are each independently selected from a hydrogen, adeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, asubstituted or unsubstituted C₁-C₆₀ alkyl group, a substituted orunsubstituted C₂-C₆₀ alkenyl group, a substituted or unsubstitutedC₂-C₆₀ alkynyl group, a substituted or unsubstituted C₁-C₆₀ alkoxygroup, a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₁₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₇-C₆₀ arylalkyl group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedC₁-C₆₀ heteroaryloxy group, a substituted or unsubstituted C₁-C₆₀heteroarylthio group, a substituted or unsubstituted C₂-C₆₀heteroarylalkyl group, a substituted or unsubstituted monovalentnon-aromatic condensed polycyclic group, a substituted or unsubstitutedmonovalent non-aromatic condensed heteropolycyclic group,—Si(Q₁)(Q₂)(Q₃), —N(Q₄)(Q₅) and —B(Q₆)(Q₇), a1 is an integer of 1 to 4,a2 to a6 are each independently an integer of 0 to 4, L₁ is selectedfrom a phenylene group, a pyridinylene group, a pyrimidinylene group, apyrazinylene group, a pyridazinylene group and a triazinylene group; anda phenylene group, a pyridinylene group, a pyrimidinylene group, apyrazinylene group, a pyridazinylene group and a triazinylene group,each substituted with at least one selected from a deuterium, —F, —Cl,—Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group,an amidino group, a hydrazine group, a hydrazone group, a carboxylicacid group or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₁-C₁₀ alkyl group, a C₁-C₁₀alkoxy group, a phenyl group, a naphthyl group, a pyridinyl group, apyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinylgroup and —Si(Q₈)(Q₉)(Q₁₀), b1 is an integer of 1 to 3, n is an integerof 0 to 3, the number of cyano groups in Formulae 1A to 1H is 2, 3 or 4,and i) one or more groups R₅ in the number of a5, and optionally, one ormore of groups R₃ in the number of a3 is a cyano group, or ii) one ormore of groups R₃ in the number of a3, one or more groups R₅ in thenumber of a5, or any combination thereof is a cyano group-substitutedC₆-C₁₀ aryl group, at least one substituent of the substituted C₁-C₆₀alkyl group, substituted C₂-C₆₀ alkenyl group, substituted C₂-C₆₀alkynyl group, substituted C₁-C₆₀ alkoxy group, substituted C₃-C₁₀cycloalkyl group, substituted C₁-C₁₀ heterocycloalkyl group, substitutedC₃-C₁₀ cycloalkenyl group, substituted C₁-C₁₀ heterocycloalkenyl group,substituted C₆-C₆₀ aryl group, substituted C₆-C₆₀ aryloxy group,substituted C₆-C₆₀ arylthio group, substituted C₇-C₆₀ arylalkyl group,substituted C₁-C₆₀ heteroaryl group, substituted C₁-C₆₀ heteroaryloxygroup, substituted C₁-C₆₀ heteroarylthio group, substituted C₂-C₆₀heteroarylalkyl group, substituted monovalent non-aromatic condensedpolycyclic group and substituted monovalent non-aromatic condensedheteropolycyclic group is selected from a deuterium, —F, —Cl, —Br, —I,—CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group,a nitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group anda C₁-C₆₀ alkoxy group; a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, aC₂-C₆₀ alkynyl group and a C₁-C₆₀ alkoxy group, each substituted with atleast one selected from a deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H,—CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₇-C₆₀ arylalkyl group, aC₁-C₆₀ heteroaryl group, a C₁-C₆₀ heteroaryloxy group, a C₁-C₆₀heteroarylthio group, a C₂-C₆₀ heteroarylalkyl group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromaticcondensed heteropolycyclic group, —Si(Q₁₁)(Q₁₂)(Q₁₃), —N(Q₁₄)(Q₁₅) and—B(Q₁₆)(Q₁₇); a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkylgroup, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, aC₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, aC₇-C₆₀ arylalkyl group, a C₁-C₆₀ heteroaryl group, a C₁-C₆₀heteroaryloxy group, a C₁-C₆₀ heteroarylthio group, a C₂-C₆₀heteroarylalkyl group, a monovalent non-aromatic condensed polycyclicgroup and a monovalent non-aromatic condensed heteropolycyclic group; aC₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₇-C₆₀arylalkyl group, a C₁-C₆₀ heteroaryl group, a C₁-C₆₀ heteroaryloxygroup, a C₁-C₆₀ heteroarylthio group, a C₂-C₆₀ heteroarylalkyl group, amonovalent non-aromatic condensed polycyclic group and a monovalentnon-aromatic condensed heteropolycyclic group, each substituted with atleast one selected from a deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H,—CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₆₀alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkylgroup, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, aC₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, aC₇-C₆₀ arylalkyl group, a C₁-C₆₀ heteroaryl group, a C₁-C₆₀heteroaryloxy group, a C₁-C₆₀ heteroarylthio group, a C₂-C₆₀heteroarylalkyl group, a monovalent non-aromatic condensed polycyclicgroup, a monovalent non-aromatic condensed heteropolycyclic group,—Si(Q₂₁)(Q₂₂)(Q₂₃), —N(Q₂₄)(Q₂₅) and —B(Q₂₆)(Q₂₇); and—Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₄)(Q₃₅) and —B(Q₃₆)(Q₃₇); and Q₁ to Q₁₀, Q₁₁ toQ₁₇, Q₂₁ to Q₂₇ and Q₃₁ to Q₃₇ are each independently selected from ahydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, a substituted or unsubstituted C₁-C₆₀ alkyl group, asubstituted or unsubstituted C₂-C₆₀ alkenyl group, a substituted orunsubstituted C₂-C₆₀ alkynyl group, a substituted or unsubstitutedC₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀ cycloalkylgroup, a substituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₇-C₆₀ arylalkyl group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedC₁-C₆₀ heteroaryloxy group, a substituted or unsubstituted C₁-C₆₀heteroarylthio group, a substituted or unsubstituted C₂-C₆₀heteroarylalkyl group, a substituted or unsubstituted monovalentnon-aromatic condensed polycyclic group and a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group.2. The condensed cyclic compound of claim 1, wherein X₁ is a singlebond.
 3. The condensed cyclic compound of claim 1, wherein ring A₁ toring A₄ are each independently selected from a benzene, a pyridine, apyrimidine, a pyrazine, a pyridazine, a naphthalene, a quinoline, anisoquinoline, a quinoxaline, a quinazoline, a cinnoline, an indene, anindole, a benzofuran, a benzothiophene, a fluorene, a carbazole, adibenzofuran and a dibenzothiophene.
 4. The condensed cyclic compound ofclaim 1, wherein ring A₁ and ring A₂ are each independently selectedfrom a benzene, a dibenzofuran and a dibenzothiophene, and ring A₃ andring A₄ are each independently selected from a benzene, a fluorene, acarbazole, a dibenzofuran and a dibenzothiophene.
 5. The condensedcyclic compound of claim 1, wherein R₁ to R₄, R_(4a) to R_(4e), R₅ to R₆and R₁₁ to R₁₃ are each independently selected from a hydrogen, adeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₁₀alkyl group and a C₁-C₁₀ alkoxy group; a C₁-C₁₀ alkyl group and a C₁-C₁₀alkoxy group, each substituted with at least one selected from adeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof and a phosphoric acid group or a salt thereof; aphenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group,a pyrazinyl group, a pyridazinyl group and a triazinyl group; a phenylgroup, a naphthyl group, a pyridinyl group, a pyrimidinyl group, apyrazinyl group, a pyridazinyl group and a triazinyl group, eachsubstituted with at least one selected from a deuterium, —F, —Cl, —Br,—I, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₁-C₁₀ alkyl group, a C₁-C₁₀alkoxy group, a phenyl group, a naphthyl group, a pyridinyl group, apyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinylgroup and —Si(Q₃₁)(Q₃₂)(Q₃₃); and —Si(Q₁)(Q₂)(Q₃), and Q₁ to Q₃ and Q₃₁to Q₃₃ are each independently selected from a hydrogen, a C₁-C₁₀ alkylgroup, a C₁-C₁₀ alkoxy group, a phenyl group, a naphthyl group, apyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinylgroup and a triazinyl group.
 6. The condensed cyclic compound of claim1, wherein R₁ to R₄, R_(4a) to R_(4e), R₅ to R₆ and R₁₁ to R₁₃ are eachindependently selected from a hydrogen, a deuterium, a cyano group, aC₁-C₁₀ alkyl group and a C₁-C₁₀ alkoxy group; a C₁-C₁₀ alkyl group and aC₁-C₁₀ alkoxy group, each substituted with at least one selected from adeuterium and a cyano group; a phenyl group, a pyridinyl group, apyrimidinyl group and a triazinyl group; a phenyl group, a pyridinylgroup, a pyrimidinyl group and a triazinyl group, each substituted withat least one selected from a deuterium, a cyano group, a C₁-C₁₀ alkylgroup, a C₁-C₁₀ alkoxy group, a phenyl group, a pyridinyl group, apyrimidinyl group, a triazinyl group and —Si(Q₃₁)(Q₃₂)(Q₃₃); and—Si(Q₁)(Q₂)(Q₃), and Q₁ to Q₃ and Q₃₁ to Q₃₃ are each independentlyselected from a hydrogen, a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, aphenyl group, a pyridinyl group, a pyrimidinyl group and a triazinylgroup.
 7. The condensed cyclic compound of claim 1, wherein L₁ isselected from a phenylene group, a pyridinylene group, a pyrimidinylenegroup and a triazinylene group; and a phenylene group, a pyridinylenegroup, a pyrimidinylene group and a triazinylene group, each substitutedwith at least one selected from a deuterium, a cyano group, a C₁-C₁₀alkyl group, a C₁-C₁₀ alkoxy group, a phenyl group, a pyridinyl group, apyrimidinyl group, a triazinyl group and —Si(Q₈)(Q₉)(Q₁₀), and Q₈ to Q₁₀are each independently selected from a hydrogen, a C₁-C₁₀ alkyl group, aC₁-C₁₀ alkoxy group, a phenyl group, a pyridinyl group, a pyrimidinylgroup and a triazinyl group.
 8. The condensed cyclic compound of claim1, wherein L₁ is selected from groups represented by Formulae 3-1 to3-40:

wherein, in Formulae 3-1 to 3-40, Z₁ is selected from a hydrogen, adeuterium, a cyano group, a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, aphenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl groupand —Si(Q₈)(Q₉)(Q₁₀), Q₈ to Q₁₀ are each independently selected from ahydrogen, a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, a phenyl group, apyridinyl group, a pyrimidinyl group and a triazinyl group, d4 is aninteger of 0 to 4, d3 is an integer of 0 to 3, d2 is an integer of 0 to2, and each of * and *′ is a binding site to a neighboring atom.
 9. Thecondensed cyclic compound of claim 1, wherein n is 0 or
 1. 10. Thecondensed cyclic compound of claim 1, wherein X₁ is a single bond, ringA₁ and A₂ are each independently selected from a benzene, a dibenzofuranand a dibenzothiophene, and at least one of ring A₁ and A₂ is a benzene,ring A₃ and A₄ are each independently selected from a benzene, afluorene, a carbazole, a dibenzofuran and a dibenzothiophene, and atleast one of ring A₃ and A₄ is a benzene, ring A₅ is a benzene, R₁ toR₄, R_(4a) to R_(4e), R₅ to R₆ are each independently selected from ahydrogen, a deuterium, a C₁-C₁₀ alkyl group and a C₁-C₁₀ alkoxy group; aC₁-C₁₀ alkyl group and a C₁-C₁₀ alkoxy group, each substituted with atleast one deuterium; a phenyl group, a pyridinyl group, a pyrimidinylgroup and a triazinyl group; a phenyl group, a pyridinyl group, apyrimidinyl group and a triazinyl group, each substituted with at leastone selected from a deuterium, a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxygroup, a phenyl group, a pyridinyl group, a pyrimidinyl group, atriazinyl group and —Si(Q₃₁)(Q₃₂)(Q₃₃); and —Si(Q₁)(Q₂)(Q₃), L₁ isselected from a phenylene group, a pyridinylene group, a pyrimidinylenegroup and a triazinylene group; and a phenylene group, a pyridinylenegroup, a pyrimidinylene group and a triazinylene group, each substitutedwith at least one selected from a deuterium, a C₁-C₁₀ alkyl group, aC₁-C₁₀ alkoxy group, a phenyl group, a pyridinyl group, a pyrimidinylgroup, a triazinyl group and —Si(Q₈)(Q₉)(Q₁₀), b1 is 1 or 2, n is 0 or1, and Q₁ to Q₃, Q₃₁ to Q₃₃, and Q₈ to Q₁₀ are each independentlyselected from a hydrogen, a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, aphenyl group, a pyridinyl group, a pyrimidinyl group and a triazinylgroup.
 11. An organic light-emitting device comprising: a firstelectrode; a second electrode; and an organic layer disposed between thefirst electrode and the second electrode, wherein the organic layercomprises an emission layer and at least one condensed cyclic compoundrepresented by Formula 1 of claim
 1. 12. The organic light-emittingdevice of claim 11, wherein the first electrode is an anode, the secondelectrode is a cathode, and the organic layer comprises a hole transportregion disposed between the first electrode and the emission layer, andan electron transport region disposed between the emission layer and thesecond electrode, wherein the hole transport region comprises at leastone selected from a hole injection layer, a hole transport layer and anelectron blocking layer, and wherein the electron transport regioncomprises at least one selected from a hole blocking layer, an electrontransport layer and an electron injection layer.
 13. The organiclight-emitting device of claim 11, wherein the emission layer comprisesthe at least one condensed cyclic compound represented by Formula
 1. 14.The organic light-emitting device of claim 11, wherein the emissionlayer comprises the at least one condensed cyclic compound representedby Formula 1 and a phosphorescent dopant, wherein an amount of the atleast one condensed cyclic compound is greater than an amount of thephosphorescent dopant.
 15. The organic light-emitting device of claim13, wherein the emission layer emits blue light.